Methanol → (S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid

HRID 841143Notes

Reaction equation

HRID 841143 reaction equation
C[O:2][C:3](=[O:55])[CH2:4][N:5]([C:16](=[O:54])[C@@H:17]([NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:18][C:19]1[N:20]=[CH:21][N:22]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=1)[CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CO.O.[OH-].[Na+]>O1CCCC1>[CH2:47]([O:46][C:44]([NH:43][C@@H:17]([CH2:18][C:19]1[N:20]=[CH:21][N:22]([C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:23]=1)[C:16]([N:5]([CH2:4][C:3]([OH:55])=[O:2])[CH2:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[O:54])=[O:45])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 69904020(S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid methyl ester

Product 1

HCID 18717554(S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acidYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Step 2 (1.8 g, 2.4 mmol) was dissolved in tetrahydrofuran (10 mL), methanol (10 mL) and water (2 mL). Sodium hydroxide (0.192 g, 4.8 mmol) was added and the mixture stirred overnight at room temperature. The solution was concentrated in vacuo and the residue taken up in 0.1 M NaPO4 buffer (100 mL). The pH was brought to 6 by the addition of 1N HCl. The product was extracted three times with ethyl acetate. The ethyl acetate was washed twice with brine, dried over MgSO4, filtered and concentrated in vacuo to give a white powder; 1.3 g (74% yield). MS-APCI: M+1=732.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe pH was brought to 6 by the addition of 1N HCl
  3. extractionThe product was extracted three times with ethyl acetate
  4. washThe ethyl acetate was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a white powder

Sources & evidence

ORD record
ord-387d583e04394accb4721f666f938215
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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