Water → HCID 67520332, compound

HRID 1923996Notes

Reaction equation

HRID 1923996 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:11][C@H:12]([NH:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([O:15]C)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[C:42]([O:41][C:39]([NH:38][CH2:37][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][C@H:12]([NH:17][C:18]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:13]([OH:15])=[O:14])=[O:40])([CH3:44])([CH3:45])[CH3:43]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86625801HCID 86625801, compound

Product 1

HCID 67520332HCID 67520332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (2S)-5-{[(tert-butoxy) carbonyl]amino}-4-({[(tert-butoxy)carbonyl]amino}methyl)-2-[(triphenylmethyl)amino]pentanoate CV (180 mg; 0.29 mmol) in methanol (15 mL) was added 4 M aq NaOH (3 mL). The mixture was stirred at r.t. for 1 h. Water (20 mL) was then added and the methanol was removed under reduce pressure. The aqueous solution was acidified with 2 M HCl to pH˜5-6 and extracted with DCM. The combined organic layers were dried over anhydrous MgSO4 and evaporated to obtain the crude (2S)-5-{[(tert-butoxy)carbonyl]amino}-4-({[(tert-butoxy)carbonyl]amino}methyl)-2-[(triphenylmethyl)amino]pentanoic acid CVI (145 mg). This material was used directly for step 6. ESIMS found for C35H45N3O6 m/z 604.4 (M+H).

Workup

  1. customthe methanol was removed
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-1273efdcfbcd44a79698c928165cb65a
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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