Acetic Acid → HCID 58092774, compound

HRID 1807661Notes

Reaction equation

HRID 1807661 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][NH:20][CH2:21][C@@:22]12[CH2:34][CH2:33][CH2:32][N:23]1[C@@H:24]([C:28]([Cl:31])([Cl:30])[Cl:29])[O:25][C:26]2=[O:27].C=O.C(O)(=O)C>ClCCCl>[F:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][N:20]([CH2:21][C@@:22]12[CH2:34][CH2:33][CH2:32][N:23]1[C@@H:24]([C:28]([Cl:30])([Cl:31])[Cl:29])[O:25][C:26]2=[O:27])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86649529HCID 86649529, compound

Product 1

HCID 58092774HCID 58092774, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (889 mg, 4.19 mmol) was added to a mixture of (3R,7aR)-7a-[(3-fluoro-benzylamino)-methyl]-3-trichloromethyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (Stage K.2, 400 mg, 1.048 mmol), formaldehyde (37% in H2O, 0.102 mL, 1.36 mmol) and acetic acid (0.150 mL, 2.62 mmol) in DCE (4 mL) under an argon atm. After 2 h stirring at rt the RM was partitioned between DCM and water. The combined organic layers were dried over Na2SO4 and evaporated to give the title compound as a pale brown oil which was used without further purification.

Workup

  1. customwas partitioned between DCM and water
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-bbcfdc9cdd6844de99ba650956b4d7d8
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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