Water → Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl ester

HRID 1841606Notes

Reaction equation

HRID 1841606 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].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:9]1[CH:10]=[CH:11][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][O:20][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:13][CH:14]=1)=[O:21])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68615769[4-(5-Hydroxy-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 86584776Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl esterYield 97.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.02 g (10.44 mmol) of [4-(5-Hydroxy-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester in 70 ml CH2Cl2 was treated at 0° C. with 0.89 ml (11.48 mmol) methanesulfonylchloride, 1.26 ml (15.66 mmol) pyridine and 1.28 g (10.44 mmol) DMAP. The reaction mixture was warmed up over night to room temperature, water (10 ml) was added and the reaction mixture was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases were washed with aqueous KHCO3 (2×), aqueous 10% NaCl, dried (Na2SO4) and evaporated to yield 3.74 g (97%) of Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl ester, mp: 85-87° C.; MS: 367 (M).

Workup

  1. extractionAfter extraction with aqueous 10% KHSO4/Et2O (3×) the organic phases
  2. washwere washed with aqueous KHCO3 (2×), aqueous 10% NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-0d89b4e2f4ce4d689e54cb1d7c76e496
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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