Acetic Acid → HCID 67591900, compound

HRID 1109773Notes

Reaction equation

HRID 1109773 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][C@H:8]1[C@@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]3[S:22][C:23]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:24]=4[N:25]=3)[CH:15]=2)[O:10][CH2:9]1)([OH:3])=[O:2].[N+](=[CH2:36])=[N-].C(O)(=O)C.O>C(OCC)C.O1CCCC1>[CH3:36][O:2][C:1]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[CH2:7][C@H:8]1[C@@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]3[S:22][C:23]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:24]=4[N:25]=3)[CH:15]=2)[O:10][CH2:9]1)=[O:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 9550DiazomethaneHCID 9956127CP-085958

Product 1

HCID 67591900HCID 67591900, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 500 mg of (+)-cis-3-(3-carboxybenzyl)-4-hydroxy-6-(5-fluorobenzothiazol-2-ylmethoxy)chroman (EPO Application 313295-A; published Oct. 17, 1988) in 10 ml of diethyl ether and 30 ml of tetrahydrofuran was added an excess of diazomethane and the reaction stirred at 0° C. for 2 hours. The reaction was allowed to warm to room temperature and 0.5 ml of acetic acid was added followed after 30 minutes by 100 ml of water and 100 ml of diethyl ether. The organic phase was washed with a brine solution, dried over sodium sulfate and concentrated to give 550 mg of a foam.

Workup

  1. temperatureto warm to room temperature
  2. washThe organic phase was washed with a brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-911a4444265e4afbb726c71dfff7c9fa
Source dataset
uspto-grants-1994_06
Patent number
US05322847

Reaction notes

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