HCID 69285697, compound → HCID 86596885, compound

HRID 1455427Notes

Reaction equation

HRID 1455427 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[CH2:26][S:27]([C:30]([CH3:33])([CH3:32])[CH3:31])(=O)=O)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C@H:13]1[CH2:26][S:27][C:30]([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 1

HCID 69285697HCID 69285697, compound

Product 1

HCID 86596885HCID 86596885, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(tert-butylsulfonylmethyl)cyclohexylcarbamate (7.3 g) in MeOH (80 mL) was charged with 10% Pd/C, Degussa (5.0 g). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 3 h and then filtered and concentrated to provide tert-butyl (1R,3R,4S)-4-amino-3-(tert-butylthiomethyl)cyclohexylcarbamate (5.0 g). MS (ES+)=349.3 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-15b553a0e1394d7c91a2492d29e878ba
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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