Water → HCID 178502730, compound

HRID 518628Notes

Reaction equation

HRID 518628 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:31][O:32][NH:33][CH3:34].O>C(Cl)Cl>[CH3:31][O:32][N:33]([CH3:34])[C:15]([C@@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 178453971HCID 178453971, compound

Product 1

HCID 178502730HCID 178502730, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid (3 g, 12.33 mmol) in DCM (35 mL) was added CDI (4.00 g, 24.66 mmol) portion-wise. The resulting mixture was stirred for 1 hour, and then O,N-dimethylhydroxylamine hydrochloride (1.804 g, 18.50 mmol) was added, and the mixture was stirred at RT for 16 hours. Water (30 mL) was added, and the mixture was stirred for 1 hour and then extracted with DCM (50 mL). The organic layer was washed with brine (30 mL), dried over sodium sulfate and concentrated to afford tert-butyl cis-4-(methoxy(methyl)carbamoyl)cyclohexylcarbamate (3.3 g, 93% yield).

Workup

  1. stirringthe mixture was stirred at RT for 16 hours
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracted with DCM (50 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7e795a531604d6183e5be3f7720d572
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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