Sodium Hydroxide → N-{2(S)-[(4-Nitrobenzylthio)acetamido]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine

HRID 1081378Notes

Reaction equation

HRID 1081378 reaction equation
C[O:2][C:3](=[O:46])[C@H:4]([CH2:42][CH2:43][S:44][CH3:45])[NH:5][C:6](=[O:41])[CH2:7][N:8]([CH2:20][C@@H:21]([NH:26][C:27](=[O:40])[CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)[C@@H:22]([CH3:25])[CH2:23][CH3:24])[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>CO>[N+:37]([C:34]1[CH:33]=[CH:32][C:31]([CH2:30][S:29][CH2:28][C:27]([NH:26][C@@H:21]([C@@H:22]([CH3:25])[CH2:23][CH3:24])[CH2:20][N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:7][C:6]([NH:5][C@H:4]([C:3]([OH:46])=[O:2])[CH2:42][CH2:43][S:44][CH3:45])=[O:41])=[O:40])=[CH:36][CH:35]=1)([O-:39])=[O:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54061835HCID 54061835, compound

Product 1

HCID 54103775N-{2(S)-[(4-Nitrobenzylthio)acetamido]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

N-{2(S)-[(4-Nitrobenzylthio)acetamido]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine methyl ester (from Example 1; 100 mg, 150 μmol) was dissolved in MeOH (1 mL) and 1.0N NaOH (300 μL, 300 μmol) was added. The mixture was stirred at 45° C. under argon for 45 minutes then the solution was partitioned between EtOAc (100 mL) and 5% citric acid (50 mL). The organic layer was washed with H2O (2×50 mL), dried (MgSO4), filtered and evaporated to give the title compound. 1H NMR; δ0.84 (t, 3H, J=7.5 Hz), 0.88 (d, 3H, J=7 Hz), 0.91-1.0 (m, 1H), 1.0-1.2 (m, 1H), 1.2-2.1 (m, 5H), 1.90 (s, 3H), 2.8-2.86 (m, 2H), 3.0-3.3 (m, 4H), 3.90 (s, 2H), 3.91-4.22 (m, 4H), 7.37-7.56 (m, 6H), 7.78-7.88 (m, 2H), 8.15 (d, 2H, J=8 Hz), 8.27 (d, 1H, J=8.3 Hz).

Workup

  1. customthe solution was partitioned between EtOAc (100 mL) and 5% citric acid (50 mL)
  2. washThe organic layer was washed with H2O (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7afce55ac46d4ee7bcc478a7f8f4e6df
Source dataset
uspto-grants-1996_12
Patent number
US05585359

Reaction notes

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