Hydrochloric Acid → HCID 67099182, compound

HRID 2076940Notes

Reaction equation

HRID 2076940 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][CH2:19][CH:20]1[CH2:25][C:24]([F:27])([F:26])[CH2:23][CH2:22][CH:21]1[CH:28]([OH:43])[CH:29]([C:35]1[CH:40]=[CH:39][C:38]([S:41][CH3:42])=[CH:37][CH:36]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:11]([O:18][CH2:19][CH:20]1[CH2:25][C:24]([F:26])([F:27])[CH2:23][CH2:22][CH:21]1[C:28](=[O:43])[CH:29]([C:35]1[CH:36]=[CH:37][C:38]([S:41][CH3:42])=[CH:39][CH:40]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67099268HCID 67099268, compound

Product 1

HCID 67099182HCID 67099182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (2.9 mL, 34 mmol) was added dropwise to a −78° C. solution of dimethyl sulfoxide (2.9 mL, 41 mmol) in CH2Cl2 (40 mL). Stirring was continued at −78° C. for an additional 10 min prior to the slow introduction down the flask wall of a solution of ethyl 3-{2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-3-hydroxy-2-[4-(methylthio)phenyl]propanoate (5.09 g, 10.6 mmol) and triethylamine (16 mL, 120 mmol) in CH2Cl2 (40 mL). The mixture was then held at −78° C. for 10 min followed by rapid warming to rt before being poured into 2 M HCl in a separatory funnel. The layers were shaken and separated, and the aqueous phase was extracted with an additional portion of CH2Cl2. The combined organics were washed with water, dried (Na2SO4) and concentrated. Flash chromatography of the residue on silica gel eluting with 1/4 ethyl acetate/hexanes afforded ethyl 3-{2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-2-[4-(methylthio)phenyl]-3-oxopropanoate as a thick, tan colored syrup.

Workup

  1. waitThe mixture was then held at −78° C. for 10 min
  2. stirringThe layers were shaken
  3. customseparated
  4. extractionthe aqueous phase was extracted with an additional portion of CH2Cl2
  5. washThe combined organics were washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1769063c28114f4e941556819b8e2068
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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