HCID 178484174, compound → HCID 178484183, compound

HRID 1254354Notes

Reaction equation

HRID 1254354 reaction equation
[F:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C@H:9]([NH:23]C(=O)OC(C)(C)C)[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH3:12])[CH2:4][CH2:3]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:23][C@@H:9]([CH2:8][C@H:5]1[CH2:4][CH2:3][C@@H:2]([F:1])[CH2:7][CH2:6]1)[CH2:10][N:11]([CH3:12])[C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 1

HCID 178484174HCID 178484174, compound

Product 1

HCID 178484183HCID 178484183, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl (S)-1-(trans-4-fluorocyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (550 mg, 1.3 mmol) in TFA/CH2Cl2 (20 mL, v/v 20%) was stirred for 1 h at rt, quenched with satd aq NaHCO3 until no further gas evolution was visible and extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and condensed under reduced pressure to obtain benzyl (S)-2-amino-3-(cis-4-fluorocyclohexyl)propylmethylcarbamate (400 mg, yield 95%). 1H NMR (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 with satd aq NaHCO3 until no further gas evolution
  2. extractionextracted with CH2Cl2 (2×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-1d91e220b3e54acf99f31e8209e6bcbd
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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