N-Carbobenzoxy-L-valine → HCID 131713305, compound

HRID 904972Notes

Reaction equation

HRID 904972 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[NH2:19][C@H:20]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:24][CH:23]=1.Cl>>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([NH:19][C@H:20]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[CH:26][CH:27]=1)=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

3

Reactant 2

HCID 726987N-Carbobenzoxy-L-valineHCID 131713306HCID 131713306, compound

Product 1

HCID 131713305HCID 131713305, compound

Conditions

Temperature
4 °C

Procedure

6.27 g (25 mmoles) of Z-Val-OH and 7.52 g (25 mmoles) of H-Tyr(But)-NH-C2H5.HCl are subjected to a condensation reaction analogously to Example 30 C. After being precipitated by means of water, the substance is dissolved in 70 ml of 95 percent strength alcohol and the solution is filtered hot and cooled (3 hours at 4° C.). The precipitate is filtered off. Yield 9.01 g (72.5%), melting point 181°, [α]D23 =-39.8° (c=1, dimethylformamide).

Workup

  1. customAfter being precipitated by means of water
  2. dissolutionthe substance is dissolved in 70 ml of 95 percent strength alcohol
  3. filtrationthe solution is filtered hot
  4. filtrationThe precipitate is filtered off
  5. customYield 9.01 g (72.5%), melting point 181°, [α]D23 =-39.8° (c=1, dimethylformamide)

Sources & evidence

ORD record
ord-613712c161cf473aa686ec121af9994f
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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