Sodium Hydroxide → HCID 54452714, compound

HRID 436958Notes

Reaction equation

HRID 436958 reaction equation
C([O:8][C:9](=[O:55])[C@H:10]([CH2:51][CH:52]([CH3:54])[CH3:53])[NH:11][C:12](=[O:50])[C@H:13]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH:14][C:15](=[O:42])[C@H:16]([CH3:41])[NH:17][C:18](=[O:40])[CH2:19][NH:20][C:21](=[O:39])[C@H:22]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])C1C=CC=CC=1.[OH-].[Na+]>CO>[C:27]([O:26][C:24]([NH:23][C@H:22]([C:21]([NH:20][CH2:19][C:18]([NH:17][C@H:16]([C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:55])=[O:8])[CH2:51][CH:52]([CH3:53])[CH3:54])=[O:50])[CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:42])[CH3:41])=[O:40])=[O:39])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=1)=[O:25])([CH3:28])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54262973HCID 54262973, compound

Product 1

HCID 54452714HCID 54452714, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

18.9 Parts N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanyl-L-phenylalanyl-L-leucine benzyl ester is dissolved in 70 parts methanol and the solution cooled to 10° C. Then, 90 parts by volume of a 1N sodium hydroxide solution is added dropwise with stirring while maintaining the temperature below 20° C. After standing at room temperature for 1 hour, the methanol is removed by evaporation under reduced pressure. The solution is washed once with ethyl ether to remove benzyl alcohol and the aqueous layer acidified with 90 parts by volume of a 1 N hydrochloric acid solution. The solid which results is filtered and washed with water to afford N-t-butoxycarbonyl-L-tyrosylglycyl-L-alanyl-L-phenylalanyl-L-leucine.

Workup

  1. temperaturewhile maintaining the temperature below 20° C
  2. customthe methanol is removed by evaporation under reduced pressure
  3. washThe solution is washed once with ethyl ether
  4. customto remove benzyl alcohol
  5. customThe solid which results
  6. filtrationis filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-a25e1183125f44359966c2df80989f8c
Source dataset
uspto-grants-1977_06
Patent number
US04028319

Reaction notes

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