Methylamine → ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrate

HRID 1721719Notes

Reaction equation

HRID 1721719 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]([OH:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].CN.C(Cl)Cl.CO>C(O)C>[NH2:3][C@@H:12]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@H:13]([OH:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 21226129Dichloromethane methanolHCID 54031650Ethyl 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxy-4-phenylbutyrate

Product 1

HCID 54193969ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Analogously to Example 23, by reacting a solution of 10.42 g of a 95:5 mixture of the (2S,3S) and (2R,3S) isomers of ethyl 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxy-4-phenylbutyrate (Example 20) in 10 ml of ethanol with 5.9 ml of a 33% solution of methylamine in ethanol there are obtained 5.39 g (82%) of ethyl (2S,3S)-3-amino-2-hydroxy-4-phenylbutyrate, TLC (SiO2, CH2Cl2 /methanol 10:1, UV254): Rf =0.34.

Sources & evidence

ORD record
ord-dcf8672f772b4c39be58e0131fcda8f3
Source dataset
uspto-grants-1996_04
Patent number
US05512688

Reaction notes

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