Formic Acid → HCID 86606486, compound

HRID 2055200Notes

Reaction equation

HRID 2055200 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH2:11]([O:18][NH:19][CH2:20][C:21]1([C:29]([OH:31])=[O:30])[CH2:26][C@H:25]([CH3:27])[CH2:24][C@H:23]([CH3:28])[CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH2:11]([O:18][N:19]([CH2:20][C:21]1([C:29]([OH:31])=[O:30])[CH2:26][C@H:25]([CH3:27])[CH2:24][C@H:23]([CH3:28])[CH2:22]1)[CH:1]=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86606485HCID 86606485, compound

Product 1

HCID 86606486HCID 86606486, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of formic acid (15.5 mL, 0.40 mol) in dichloromethane (75 mL) at 0° C. under a nitrogen atmosphere was added acetic anhydride (5.9 mL, 62 mmol). After 1 h, a solution of (3S,5R)-1-(Benzyloxyamino-methyl)-3,5-dimethyl-cyclohexanecarboxylic acid (1.8 g, 6.2 mmol) in dichloromethane (75 mL) was added. The reaction was stirred at room temperature for 18 h and was concentrated in vacuo. Water (150 mL) was added and the mixture was extracted with dichloromethane (75 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a yellow solid (1.59 g, 80%). MH+320.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionWater (150 mL) was added
  3. extractionthe mixture was extracted with dichloromethane (75 mL×5)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-1ace69baf9204e26ba440378a91edba1
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

Loading…