Thioglycolic Acid → HCID 19900352, compound

HRID 1029455Notes

Reaction equation

HRID 1029455 reaction equation
C1(CO[CH:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:21][CH:20]=2)[CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)C=CC=CC=1.[C:37]([OH:41])(=[O:40])[CH2:38][SH:39].B(F)(F)F.O(CC)CC>C(Cl)Cl>[C:13]1([CH2:12][O:11][CH2:10][CH:9]([S:39][CH2:38][C:37]([OH:41])=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:21][CH:20]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 8000Boron trifluoride etherateHCID 44278819HCID 44278819, compound

Product 1

HCID 19900352HCID 19900352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of the ether (151 mg) (Step 2) and thioglycolic acid (31 μL) in CH2Cl2 at 0° C. was added BF3 /OEt2 (117 μL) dropwise. The mixture was stirred at 0° C. for 1 h and poured onto 25% aqueous NH4OAc, extracted with CH2Cl2 and the organic phase was dried and evaporated. Chromatography on silica gel using ethyl acetate/hexane containing 0.1% AcOH afforded the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. customthe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-7e599eb3c76b4967a3ecfb34826cfafd
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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