Trifluoroacetic acid → N-[(1S,2S)-2-Benzyloxy-2-[(3R,6S)-6-(3-cyclopentylpropoxy)-morpholin-3-yl]-1-(3,5-difluorobenzyl)-ethyl]-acetamide trifluoroacetate

HRID 20338Notes

Reaction equation

HRID 20338 reaction equation
C(OC([N:8]1[C@@H:13]([C@@H:14]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:15]([NH:25][C:26](=[O:28])[CH3:27])[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:12][O:11][C@H:10]([O:37][CH2:38][CH2:39][CH2:40][CH:41]2[CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:9]1)=O)(C)(C)C.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>ClCCl>[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49].[CH2:30]([O:29][C@H:14]([C@H:13]1[CH2:12][O:11][C@H:10]([O:37][CH2:38][CH2:39][CH2:40][CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45]2)[CH2:9][NH:8]1)[C@@H:15]([NH:25][C:26](=[O:28])[CH3:27])[CH2:16][C:17]1[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68564195HCID 68564195, compound

Product 1

HCID 68564389N-[(1S,2S)-2-Benzyloxy-2-[(3R,6S)-6-(3-cyclopentylpropoxy)-morpholin-3-yl]-1-(3,5-difluorobenzyl)-ethyl]-acetamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2S,5R)-5-[(1S,2S)-2-Acetylamino-1-benzyloxy-3-(3,5-difluorophenyl)-propyl]-2-(3-cyclopentylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (67 mg, 0.106 mmol) in neat trifluoroacetic acid under nitrogen. After 20 min, dilute the reaction mixture with dichloromethane and concentrate it on the rotary evaporator four times, then dilute with benzene and concentrate again. Dry the residue under vacuum to give the title compound.

Workup

  1. concentrationconcentrate it
  2. customon the rotary evaporator four times
  3. additiondilute with benzene
  4. concentrationconcentrate again
  5. customDry the residue under vacuum

Sources & evidence

ORD record
ord-e0288f93b5b84803856ffcecac1c817a
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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