Chloroform → HCID 53848962, compound

HRID 1720796Notes

Reaction equation

HRID 1720796 reaction equation
Cl.[C:2]([O:6][C:7](=[O:29])[C@H:8]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=1)([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.Cl[CH2:38][CH2:39][S:40](Cl)(=[O:42])=[O:41].C(Cl)(Cl)Cl>ClCCl>[C:2]([O:6][C:7](=[O:29])[C@H:8]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][S:40]([CH:39]=[CH2:38])(=[O:42])=[O:41])=[CH:13][CH:12]=1)([CH3:4])([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 67768754HCID 67768754, compound

Product 1

HCID 53848962HCID 53848962, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(aminomethyl)benzoyl-glutamic acid di-t-butyl ester hydrochloride as obtained in Reference Example 37 (255 mg) and triethylamine (0.27 ml) were dissolved in dichloromethane (4 ml). To this solution, a solution of chloroethylsulfonyl chloride (161 mg) in dichloromethane (4 ml) was added drop by drop under ice cooling conditions over a period of about 15 minutes, followed by stirring at the same ternperature for 30 minutes. To the mixture, ice water (12 ml). and chloroform (10 ml) were added, followed by vigorous stirring, after which the organic layer was separated, and concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol:chloroform=1:99) to yield the title compound (172 mg, yield 58.3%) as a colorless solid.

Workup

  1. customafter which the organic layer was separated
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (methanol:chloroform=1:99)

Sources & evidence

ORD record
ord-21f638a8404446ed9eb1924321b9bb8e
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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