[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester → [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](phthalimidomethyl)phosphinic acid

HRID 476694Notes

Reaction equation

HRID 476694 reaction equation
C[O:2][P:3]([CH2:17][CH:18]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:19][C:20](C)([CH3:22])[CH3:21])([CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])=[O:4]>C(O)(=O)C.Br>[CH3:21][CH:20]([CH3:22])[CH2:19][CH:18]([C:24](=[O:35])[NH:25][C@H:26]([C:31](=[O:34])[NH:32][CH3:33])[CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:17][P:3]([CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])(=[O:2])[OH:4]

Participants

4

Reactant 1

HCID 54363570[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester

Product 1

HCID 53958545[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](phthalimidomethyl)phosphinic acidYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

123 mg of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester were dissolved in a mixture of 3 ml of acetic acid and 3 ml of 48% hydrogen bromide in acetic acid and the mixture was left to stand at room temperature for 18 hours. The solvent was removed by evaporation, the residue was dissolved in a mixture of 10 ml of toluene and 5 ml of acetone and the solution was evaporated. This procedure was repeated twice and the residue was then dissolved in a mixture of 5 ml of dichloromethane and 3 ml of acetone and the solution was evaporated. After drying under a high vacuum (0.1 mmHg), there were obtained 115 mg of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](phthalimidomethyl)phosphinic acid in the form of an off-white foam.

Workup

  1. waitthe mixture was left
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in a mixture of 10 ml of toluene and 5 ml of acetone
  4. customthe solution was evaporated
  5. dissolutionthe residue was then dissolved in a mixture of 5 ml of dichloromethane and 3 ml of acetone
  6. customthe solution was evaporated
  7. customAfter drying under a high vacuum (0.1 mmHg)

Sources & evidence

ORD record
ord-eb235a0b208c443eb88281972837aef2
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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