Water → HCID 178486043, compound

HRID 2057257Notes

Reaction equation

HRID 2057257 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]#[C:16][CH2:17][O:18][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:13][CH2:14]1)=[O:19])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178486040HCID 178486040, compound

Product 1

HCID 178486043HCID 178486043, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 520 mg (1.95 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 14 ml CH2Cl2 was treated at 0° C. with 0.17 ml (2.14 mmol) methanesulfonylchloride, 0.235 ml (2.92 mmol) pyridine and 238 mg (1.95 mmol) DMAP. The reaction mixture was warmed up over night to room temperature, water (2 ml) was added and the reaction was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 435 mg (65%) of trans-Methanesulfonic acid 3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-prop-2-ynyl ester, MS: 345 (M).

Workup

  1. extractionAfter extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases
  2. washwere washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-bb7d179b9a524788a5c3f75340f3b400
Source dataset
uspto-grants-2008_02
Patent number
US07335687B2

Reaction notes

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