Hydrazine hydrate (1:1) → (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate

HRID 476712Notes

Reaction equation

HRID 476712 reaction equation
[CH2:1]([O:3][P:4]([CH2:18][CH:19]([C:25](=[O:36])[NH:26][C@H:27]([C:32](=[O:35])[NH:33][CH3:34])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:20][C:21](C)([CH3:23])[CH3:22])([CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O)=[O:5])[CH3:2].[OH2:37].NN>C(O)C>[C:32]([OH:35])(=[O:37])[CH3:27].[CH2:1]([O:3][P:4]([CH2:6][NH2:7])([CH2:18][CH:19]([C:25](=[O:36])[NH:26][C@H:27]([C:32](=[O:35])[NH:33][CH3:34])[CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54291077[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid ethyl ester

Product 1

HCID 86743561(aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid ethyl ester were treated in a manner analogous to that described in Example 2(A)(i), with the exception that a 0.33M solution of hydrazine hydrate in ethanol was used, to give 2.06 g of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester acetate in the form of a white foam.

Sources & evidence

ORD record
ord-15e45523124d44a58d637999ce4adcd0
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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