Triethylamine → HCID 57659779, compound

HRID 1011593Notes

Reaction equation

HRID 1011593 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:21])([F:20])[C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl.[OH:23][C@H:24]1[CH2:28][NH:27][C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:25]1>ClCCl.CCOC(C)=O>[OH:23][C@H:24]1[CH2:28][N:27]([S:16]([C:13]2[CH:14]=[CH:15][C:10]([C:9]([F:21])([F:20])[F:8])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:25]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

Product 1

HCID 57659779HCID 57659779, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (TEA) (15.34 ml, 110.1 mmol) and 4-(trifluoromethyl)benzene-1-sulfonyl chloride (8.97 g, 36.7 mmol) were added to a solution of (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride (2) (6.59 g, 36.7 mmol) in dichloromethane (150 ml) in an ice bath. The mixture was warmed to room temperature and stirred overnight at RT., concentrated reaction in vacuo, dissolved in EtOAc and washed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine. The organic layers were dried with sodium sulfate and concentrated in vacuo to yield (2S,4R)-methyl 4-hydroxy-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylate) (3) (9.55 g, 73%) as a white semi-solid, which was used without further purification in the next step. MS m/z 376.1 (M+Na)+; retention time=1.691 min, method [1].

Workup

  1. concentration, concentrated
  2. customreaction in vacuo
  3. washwashed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a1ab7d33b2f4a1f97fe951e279b1a73
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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