Sodium Hydroxide → HCID 53967500, compound

HRID 393476Notes

Reaction equation

HRID 393476 reaction equation
C[O:2][C:3](=[O:50])[C@H:4]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:32](=[O:33])[CH:31]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]([C:41](=[O:43])[CH3:42])[CH:29]2[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:24][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH-].[Na+]>CCO.CC(O)=O>[C:41]([N:30]1[CH:31]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:32](=[O:33])[N:28]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][C@@H:4]([C:3]([OH:50])=[O:2])[NH:5][C:6]([C:8]3([CH2:13][CH2:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12]3)=[O:7])=[CH:23][CH:24]=2)[CH:29]1[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)(=[O:43])[CH3:42]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54344269HCID 54344269, compound

Product 1

HCID 53967500HCID 53967500, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

4-(3-acetyl-5-oxo-2-phenyl-4-phenylmethyl-1-imidazolidinyl)-N-[[1-[4-(methylsulfonyl)butyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester diastereomer 1(90 mg, 0.128 mmol) in EtOH (3 mL) was treated with NaOH (1N, 0.3 mL) at room temperature for 30 min. The resulting solution was acidified with 1 drop of HOAc and was purified by HPLC (C-18, linear gradent from 5% acetonitrile to 95% in water over 30 min) to give 84 mg (95%, 0.122 mmol) of 4-(3-acetyl-5-oxo-2-phenyl-4-phenylmethyl-1-imidazolidinyl)-N-[[1-[4-(methyl-sulfonyl)butyl]cyclopentyl]carbonyl]-L-phenylalanine diastereomer 1. LR MS: 688 (M+H).

Workup

  1. customwas purified by HPLC (C-18, linear gradent from 5% acetonitrile to 95% in water over 30 min)

Sources & evidence

ORD record
ord-3716b860dbdd4e52a768d5be49c3535d
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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