Triethylamine → methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(methanesulfonyl-oxymethyl)tetrahydrofuran-3-yl]benzoate

HRID 927922Notes

Reaction equation

HRID 927922 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([NH:9][C:10]1[C:19]([C@H:20]2[CH2:24][CH2:23][O:22][C@H:21]2[CH2:25][OH:26])=[CH:18][CH:17]=[C:16]([NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:6]([NH:9][C:10]1[C:19]([C@H:20]2[CH2:24][CH2:23][O:22][C@H:21]2[CH2:25][O:26][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:18][CH:17]=[C:16]([NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70983847methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate2×

Product 1

HCID 86713287methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(methanesulfonyl-oxymethyl)tetrahydrofuran-3-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.042 mL) was added to a mixture of methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)-tetrahydrofuran-3-yl]benzoate (Intermediate 32, 0.14 g) and triethylamine (0.15 mL) in DCM (5 mL) and the resultant mixture was stirred at room temperature for 30 minutes. The mixture was washed with 1M hydrochloric acid, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(methanesulfonyloxymethyl)-tetrahydrofuran-3-yl]benzoate (0.166 g) as a gum.

Workup

  1. washThe mixture was washed with 1M hydrochloric acid
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f93da9938f7e4a05bef390f52c3205b5
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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