4-Toluenesulfonyl chloride → HCID 86678440, compound

HRID 1473724Notes

Reaction equation

HRID 1473724 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][CH2:18][CH:19]([CH2:25][CH2:26][CH2:27][OH:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>ClCCl>[CH2:23]([O:22][C:20](=[O:21])[CH:19]([CH2:25][CH2:26][CH2:27][O:28][S:42]([C:39]1[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=1)(=[O:44])=[O:43])[CH2:18][CH2:17][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH3:24]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 866784391-tert-Butyl 6-ethyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-hydroxypropyl)hexanedioate

Product 1

HCID 86678440HCID 86678440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

190 mg (0.47 mmol) of 1-tert-Butyl 6-ethyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-hydroxypropyl)hexanedioate (5b) were dissolved in 10 mL dichloromethane at 0° C. Then, 284 mg (391 microL, 2.8 mmol) triethylamine and 179 mg (0.94 mmol) p-toluene sulfonyl chloride were added at 0° C. and the mixture was stirred at this temperature for 3 h. After stirring for 18 h at r.t. the solution was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate gradient) to give (S)-2-tert-Butoxycarbonylamino-5-[3-(toluene-4-sulfonyloxy)-propyl]-hexanedioic acid 1-tert-butyl ester 6-ethyl ester as a colourless oil.

Workup

  1. stirringAfter stirring for 18 h at r.t. the solution
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-bb7e5887172d47dfa2b032d7dad7230b
Source dataset
uspto-grants-2015_04
Patent number
US09017645B2

Reaction notes

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