Triethylamine → HCID 59512307, compound

HRID 1158372Notes

Reaction equation

HRID 1158372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][OH:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([CH2:34][O:35][S:44]([CH3:43])(=[O:46])=[O:45])[C@H:11]([CH2:13][N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59512299(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59512307HCID 59512307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4R)-3-hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.32 g, 4.69 mmol; Example 10, reaction step H) is subsequently added at −20° C. with stirring NEt3 (1.95 mL, 14.1 mmol) and in a dropwise fashion methane sulfonylchloride (0.423 mL, 5.39 mmol). Stirring is continued for 20 min at −20° C., the mixture is then diluted with CH2Cl2 and the organic layer is washed with 2N HCl, dried (Na2SO4) and evaporated to dryness to give the crude title compound as yellowish oil. TLC, Rf (hexane/AcOEt 1:3)=0.13.

Workup

  1. washthe organic layer is washed with 2N HCl
  2. dry with materialdried (Na2SO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-42e7aafd6d794b1bb9be995cd2c9cba3
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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