Ethyl chloroformate → HCID 15288031, compound

HRID 37715Notes

Reaction equation

HRID 37715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][C:20]4[S:21][C:22]5[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)=[CH:15][CH:16]=3)[C:11]([CH2:29][C:30](O)=[O:31])=[C:10]2[CH3:33])=[CH:4][CH:3]=1.ClC(OCC)=O.[OH-].[NH4+:41]>O1CCCC1.C(N(CC)CC)C.O>[S:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[CH2:19][O:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]([CH3:33])=[C:11]2[CH2:29][C:30]([NH2:41])=[O:31]

Participants

7

Reactant 3

HCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 152880251-[(4-Chlorophenyl)methyl]-2-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid

Product 1

HCID 15288031HCID 15288031, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture containing the compound of Example 37(0.5 g, 1.05 mmol) in tetrahydrofuran (30 mL) and triethylamine (0.6 mL) at -10° C., is added slowly with stirring a solution of ethyl chloroformate (0.14 g, 1.29 mmol) in tetrahydrofuran (10 mL). After 30 minutes, 30% ammonium hydroxide (0.6 mL) is added and the mixture is stirred for 18 hours at 23° C. The mixture is diluted with water (100 mL) and is extracted with ethyl acetate (3×100 mL). The combined extract is washed with 2N HCl (200 mL) and brine (200 mL), dried over MgSO4 and concentrated to give crude product (0.55 g). Crystallization from acetonitrile gives pure title compound in 90% yield as a white solid, m.p. 169°-170° C.

Workup

  1. additionis added slowly
  2. extractionis extracted with ethyl acetate (3×100 mL)
  3. extractionThe combined extract
  4. washis washed with 2N HCl (200 mL) and brine (200 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give crude product (0.55 g)
  8. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-194e5ca4f5c94a018c65a004d4b879c9
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Reaction notes

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