Acetic Acid → HCID 11974441, compound

HRID 1172347Notes

Reaction equation

HRID 1172347 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH2:11][C@H:10]1[C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][C:13]([C:15]([O:17][CH3:27])=[O:16])=[CH:12][CH2:11][C@@H:10]1[C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=1[F:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 68769741HCID 68769741, compound

Product 1

HCID 11974441HCID 11974441, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 39A (510 mg) was dissolved in methanol (1 mL) and CH2Cl2 (1 mL), and then (trimethylsilyl)diazomethane solution (0.4 mL, 2M in ether) was added. After ten minutes, acetic acid (0.2 mL) was added. The mixture was concentrated, filtered through a silica gel plug, and purified by chromatography (Column: Chiralcel AD, Mobile Phase: hexane/ethanol/methanol=95/2.5/2.5) to give the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.31 (s, 9H), 2.18-2.28 (m, 1H), 2.41-2.50 (m, 1H), 2.57-2.67 (m, 1H), 2.86 (d, J=16.48 Hz, 1H), 3.10-3.18 (m, 1H), 3.76 (s, 3H), 4.02 (s, 1H), 4.37 (d, J=7.63 Hz, 1H), 6.86-6.94 (m, 1H), 6.99 (s, 1H), 7.11 (s, 1H). MS (DCI) m/z 403 (M+NH4)+.

Workup

  1. waitAfter ten minutes
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered through a silica gel plug
  4. custompurified by chromatography (Column: Chiralcel AD, Mobile Phase: hexane/ethanol/methanol=95/2.5/2.5)

Sources & evidence

ORD record
ord-d9ef3a3810dc4c279dc786ac08d96085
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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