Lithium Hydroxide → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-cyanophenylmethyl)-hexanoic acid

HRID 263769Notes

Reaction equation

HRID 263769 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=2)[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:32].[Li+]>C(COC)OC.O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=1)[C:20]([OH:22])=[O:32])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 677189595(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-cyanophenylmethyl)-dihydrofuran-2-(3H)-one

Product 1

HCID 228742915(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(m-cyanophenylmethyl)-hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 1i), 1.6 g (3.8 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(m-cyanophenylmethyl)-dihydrofuran-2-(3H)-one in 37 ml of dimethoxyethane and 20 ml of water are hydrolysed with 15.2 ml of 1M lithium hydroxide solution to yield the title compound: tRet (I)=13.8 min.

Sources & evidence

ORD record
ord-8f7494242561468eb611badd14a40869
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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