Trifluoroacetic acid → HCID 20729748, compound

HRID 352175Notes

Reaction equation

HRID 352175 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:20]([O:19][C:17](=[O:18])[NH:16][CH2:15][C@@H:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22713895[3-(Benzyloxycarbonylamino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 20729748HCID 20729748, compound

Procedure

S-amino enantiomer of N-({3-[(t-butoxy)carbonyl-amino]cyclohexyl}methyl) (phenylmethoxy)carboxamide (1.0 g, 2.76 mmol) was treated with TFA (5 mL) under N2. After 20 min of stirring at r.t. the reaction was complete. The crude was then concentrated to an oil which was purified on a Varian Bond-Elut SCX column (10 g). The column was eluted consecutively with CHCl3, MeOH, and ammonia (2.0M in MeOH). The pure product was recovered from the ammonia fractions. The solvent was removed in vacuo to afford 0.632 g (87%) as a colorless oil. MS (ES+) m/z 263.0 (M+H)+.

Workup

  1. concentrationThe crude was then concentrated to an oil which
  2. customwas purified on a Varian Bond-Elut SCX column (10 g)
  3. washThe column was eluted consecutively with CHCl3, MeOH, and ammonia (2.0M in MeOH)
  4. customThe pure product was recovered from the ammonia fractions
  5. customThe solvent was removed in vacuo
  6. customto afford 0.632 g (87%) as a colorless oil

Sources & evidence

ORD record
ord-dd66de9effbc43ffa8f6b4d193a621bb
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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