HCID 178444651, compound → HCID 178484308, compound

HRID 847576Notes

Reaction equation

HRID 847576 reaction equation
[CH3:1][N:2]([C:14]([O:16][C@@H:17]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:18]([N:20]([CH3:46])[C@H:21]([C:28]([NH:30][C@H:31]([C@@H:39]([OH:45])[CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:29])[CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1)=[O:19])=[O:15])[CH2:3][CH2:4][N:5](C(OC(C)(C)C)=O)[CH3:6]>FC(F)(F)C(O)=O>[CH3:1][N:2]([C:14]([O:16][C@@H:17]([CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:18]([N:20]([CH3:46])[C@H:21]([C:28]([NH:30][C@H:31]([C@@H:39]([OH:45])[CH2:40][CH2:41][CH:42]([CH3:43])[CH3:44])[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:29])[CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1)=[O:19])=[O:15])[CH2:3][CH2:4][NH:5][CH3:6]

Participants

3

Reactant 1

HCID 178444651HCID 178444651, compound

Product 1

HCID 178484308HCID 178484308, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2(S)-[Nα -[2(S)-[N-methyl-N-{2-(N-t-butoxycarbonyl-N-methylamino)ethyl}aminocarbonyloxy]-3-phenylpropionyl]-Nα -methyl-L-histidyl]amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (114 mg) in trifluoroacetic acid (10 ml) was stirred at 0° C. for 1 hour. After evaporation of the solvent, the residue was dissolved in ethyl acetate (20 ml) and the solution was washed with 1 M sodium bicarbonate solution and water successively, and dried over magnesium sulfate. Evaporation of the solvent gave 2(S)-[Nα -[2(S)-{N-methyl-N-(2-methylaminoethyl)aminocarbonyloxy}-3-phenylpropionyl]-Nα -methyl-L-histidyl]amino-1-cyclohexyl-3(S)-hydroxy-6-methylheptane (88 mg) as an amorphous powder.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washthe solution was washed with 1 M sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7d910796ec35415b8db5c06d90f1620a
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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