ChemicalBook CAS DataBase List (R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid

(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid synthesis

5synthesis methods

Product Name:(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid
CAS Number:123673-31-4
Molecular formula:C12H15NO5
Molecular Weight:253.25

(R)-benzyl 2,5-dioxotetrahydrofuran-3-ylcarbamate

75443-62-8
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$112.00/100mg

(R)-3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid

123673-31-4
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Yield:123673-31-4 85%

Reaction Conditions:

Stage #1: benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamatewith sodium tetrahydroborate in tetrahydrofuran at 0 - 25; for 6 h;
Stage #2: with hydrogenchloride;water in tetrahydrofuran at 0; pH=4;

Steps:

2; 4 (R)-3-(benzyloxycarbonylamino)-4-hydroxybutanoic acid

A solution of (R)-benzyl 2,5-dioxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 1, 53.28 g, 213.79 mmol) in THF (330 ml) was added over a 4 hour period using an additional funnel to a mixture of sodium borohydride (8.09 g, 213.79 mmol) in THF (330 ml) at 0° C. After the addition was complete, the mixture was warmed to room temperature and stirred for 2 hours. The solution was then concentrated under reduced pressure to ? of the original volume, cooled to 0° C., and carefully quenched by the slow addition of water (400 ml). The mixture was acidified to pH 4 with 1N aqueous hydrochloric acid and extracted with Et₂O (5×300 ml). The combined organic layers were dried (Na₂SO₄) and concentrated in vacuo to provide the title product (45.9 g, yield: 85%).¹H NMR (300 MHz, METHANOL-d₄) δ ppm 2.41-2.54 (m, 1H) 2.56-2.70 (m, 1 H) 3.33 (dt, 2H) 3.42-3.65 (m, 2H) 3.95-4.12 (m, 1H) 5.01-5.22 (m, 2H) 7.14-7.46 (m, 5 H).LCMS: (ESI) m/z 254.1 [M+H]⁺.Optical Rotation:Concentration: 0.14 g/dLLamp: SodiumWavelength: 589 nmTemperature: 20° C.Path length: 10 cm Cell volume: 1 ml Solvent: CH₂Cl₂[α]=+13

References:

US2012/35134,2012,A1 Location in patent:Page/Page column 9; 32

78663-07-7
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$5.00/1g

123673-31-4
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References

Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate

87219-29-2
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$7.00/100mg

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References

4515-23-5 Synthesis

4515-23-5
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$15.00/1g

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References

Carbamic acid, [1-[1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxyethyl]-3-oxo-3-[(phenylmethyl)amino]propyl]-, phenylmethyl ester, [S-(R*,S*)]- (9CI)

135517-09-8
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123673-31-4
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References