Hydrochloric Acid → N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycine

HRID 1156953Notes

Reaction equation

HRID 1156953 reaction equation
[NH:1]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([O:25]CC)=[O:24])=[O:20])[CH2:15][CH2:16][S:17][CH3:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH-].[Na+].Cl.CN(C=O)C>CO>[NH:1]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[CH2:15][CH2:16][S:17][CH3:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 12919643BOC-Tyr-(D)-Met-Gly-OEt

Product 1

HCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycineYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 ml of MeOH is dissolved 2.8 g of BOC-Tyr-(D)-Met-Gly-OEt. After cooling, 12 ml of N-aqueous sodium hydroxide solution is added, and the mixture is stirred at room temperature for 1 hour. After cooling, 60 ml of 0.2 N-aqueous hydrochloric acid solution is added, and the precipitated crystals are collected by filtration, followed by washing with cold water. Thus obtained is 2.3 g of the desired product, m.p. 184°-186° C., Rf1 =0.24, [α]D21 +13.3° (c=0.46, DMF).

Workup

  1. temperatureAfter cooling
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals are collected by filtration
  4. washby washing with cold water
  5. customThus obtained

Sources & evidence

ORD record
ord-c437ccb51a554d7b9aab152ea11cdfa4
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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