HCID 178484174, compound → HCID 178484184, compound

HRID 1254356Notes

Reaction equation

HRID 1254356 reaction equation
C(OC([NH:8][C@@H:9]([CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([F:30])[CH2:26][CH2:25]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:8][C@@H:9]([CH2:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([F:30])[CH2:28][CH2:29]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 1

HCID 178484174HCID 178484174, compound

Product 1

HCID 178484184HCID 178484184, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of benzyl (S)-2-(t-butoxycarbonylamino)-3-(trans-4-fluorocyclohexyl)-propyl(methyl)carbamate (200 mg, 0.47 mmol) in TFA/CH2Cl2 (15 mL, v/v 20%) was stirred for 1 h at rt, then quenched by addition of sat'd aq NaHCO3 solution until gas evolution ceased. The mixture was extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to obtain benzyl (S)-2-amino-3-(trans-4-fluorocyclohexyl)propyl(methyl)carbamate (140 mg, yield 93%). 1HNMR (CDCl3, 400 MHZ): δ 1.42(m, 4 H), 1.64(m, 4 H), 2.98(d, 3 H), 3.21(m, 1 H), 3.50(m, 1 H), 3.90(m, 1 H), 5.13(d, 2 H), 7.33(m, 5 H).

Workup

  1. customquenched by addition of sat'd aq NaHCO3 solution until gas evolution
  2. extractionThe mixture was extracted with CH2Cl2 (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5b206b72b0e4554a45129e302309587
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

Loading…