Hydrazine hydrate (1:1) → ZTyr(Bz)D-AlaNHNH2

HRID 542644Notes

Reaction equation

HRID 542644 reaction equation
[OH2:1].[NH2:2][NH2:3].CO[C:6](=[O:39])[C@@H:7]([CH3:38])[NH:8][C:9](=[O:37])[C@H:10]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C(O)C.O1CCCC1>[NH:11]([C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C@H:10]([C:9]([NH:8][C@@H:7]([C:6]([NH:2][NH2:3])=[O:39])[CH3:38])=[O:37])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][C:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:1])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13850973(N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-D-alanine methyl ester

Product 1

HCID 131714293ZTyr(Bz)D-AlaNHNH2

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydrazine hydrate (5.05 ml.) in ethanol (45 ml.) was added to a solution of (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-D-alanine methyl ester (15.18 g.) in tetrahydrofuran (135 ml.). The resulting solution was stirred at room temperature and seeded. (N-Benzyloxycarbonyl-O-benzyl-L-tyrosyl)-D-alanyl hydrazide (13.2 g.; m.r. 216°-218° C.; [α]D25 -21.4°, c=2, dimethylformamide) separated from the solution as a crystalline solid.

Workup

  1. custom(N-Benzyloxycarbonyl-O-benzyl-L-tyrosyl)-D-alanyl hydrazide (13.2 g.; m.r. 216°-218° C.; [α]D25 -21.4°, c=2, dimethylformamide) separated from the solution as a crystalline solid

Sources & evidence

ORD record
ord-b88979d1e2ed4f4185aea3ddb7b246ae
Source dataset
uspto-grants-1987_04
Patent number
US04658013

Reaction notes

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