HCID 11550556, compound → HCID 131714618, compound

HRID 236463Notes

Reaction equation

HRID 236463 reaction equation
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19](O)=[O:20])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:32][C@H:33]([C:42]([CH2:44][Cl:45])=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1.Cl.N(C(OCC1C=CC=CC=1)=O)[C@H](C(NCC(N[C@H](C(N[C@H](C(CCl)=O)CC(C)C)=O)CC(C)C)=O)=O)CC1C=CC=CC=1>>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:19]([NH:32][C@H:33]([C:42]([CH2:44][Cl:45])=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)=[O:20])[CH3:18])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 11550556HCID 11550556, compoundHCID 131714616HCID 131714616, compoundHCID 131714619HCID 131714619, compound

Product 1

HCID 131714618HCID 131714618, compound

Procedure

Z-Phe-Gly-Ala-OH (0.77 g, 1.80 mmol) was coupled to H-TyrCH2Cl.HCl by a mixed anhydride coupling procedure substantially similar to that described for preparation of Z-Phe-Gly-Leu-LeuCH2Cl in Procedure C, above. Product was crystallized from ethyl acetate to yield 0.73 g of Z-Phe-Gly-Ala-TyrCH2Cl. Product slowly decomposed at 140°-160° and melted with complete decomposition at 160°-160.5°.

Workup

  1. customProduct was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2f2dd5c75ba4486f906e5fd5a3c34b23
Source dataset
uspto-grants-1987_02
Patent number
US04644055

Reaction notes

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