Sodium Hydroxide → HCID 54048888, compound

HRID 372776Notes

Reaction equation

HRID 372776 reaction equation
C([O:8][C:9](=[O:57])[C@H:10]([CH2:53][CH2:54][S:55][CH3:56])[NH:11][C:12](=[O:52])[C@H:13]([CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)[NH:14][C:15](=[O:41])[CH2:16][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][CH2:16][C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:57])=[O:8])[CH2:53][CH2:54][S:55][CH3:56])=[O:52])[CH2:42][C:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45][CH:44]=1)=[O: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])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54293522HCID 54293522, compound

Product 1

HCID 54048888HCID 54048888, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

21.1 Parts N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-tryptophyl-L-methionine benzyl ester is dissolved in 70 parts methanol and the solution cooled to 10° C. Then, 90 parts by volume of 1 N 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 1 N hydrochloric acid. The solid which results is filtered and washed with water to afford N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-tryptophyl-L-methionine.

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-c362007cee2146d6aeb8de4b239eb2e1
Source dataset
uspto-grants-1978_05
Patent number
US04092304

Reaction notes

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