Hydrochloric Acid → methanesulfonic acid (2S,4R)-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl ester

HRID 1006782Notes

Reaction equation

HRID 1006782 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][C@H:17]([S:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:15]1[CH2:39][OH:40])(=[O:13])=[O:12].[CH3:41][S:42](Cl)(=[O:44])=[O:43].N1C=CC=CC=1.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][C@H:17]([S:19][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:16][C@H:15]1[CH2:39][O:40][S:42]([CH3:41])(=[O:44])=[O:43])(=[O:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 69431241(2S,4R)-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methanol

Product 1

HCID 86584832methanesulfonic acid (2S,4R)-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl esterYield 99.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

A solution of 14.14 g (25 mmol) of (2S,4R)-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methanol in 300 ml CH2Cl2 was treated at 0° C. with 2.14 ml (27.7 mmol) methane sulfonylchloride, 3.02 ml (37.5 mmol) pyridine, 3.05 g (25 mmol) DMAP and stirred at room temperature for 4 h. The reaction mixture was poured into EtOAc/H2O acidified with 1 N HCl. The organic phase was washed with 10% aqueous NaCl, dried over Na2SO4 and evaporated to give 15.98 g (99%) of methanesulfonic acid (2S,4R)-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl ester, MS: 644 (MH+).

Workup

  1. washThe organic phase was washed with 10% aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-42d7c45535954da5be2160d77fe4f97e
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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