HCID 178444651, compound → HCID 178484308, compound

HRID 1588836Notes

Reaction equation

HRID 1588836 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 1M 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 1M sodium bicarbonate solution and water successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a84d235540a2455b81dc9c5344dd807b
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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