Benzyl Alcohol → (N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester

HRID 1721619Notes

Reaction equation

HRID 1721619 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[CH3:17][O:18][C:19](=[O:28])[CH:20]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[NH:21][CH3:22].C(N(CC)CC)C.Cl.[Cl-].[Na+]>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:28])[CH:20]([CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[N:21]([S:2]([NH:5][C:6]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])(=[O:4])=[O:3])[CH3:22]

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 867494602-(3-Methylbutyl)-sarcosine methyl ester hydrochloride

Product 1

HCID 18922249(N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl esterYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5.77 ml (66.78 mmol) of chlorosulfonyl isocyanate in methylene chloride was added, under nitrogen, benzyl alcohol (6.89 ml, 66.57 mmol) at 0°-5° C. After stirring the above solution for 1 hour, a solution of 13.166 g (62.78 mmol) of 2-(3-methylbutyl)-sarcosine methyl ester hydrochloride in methylene chloride containing triethylamine (27.33 ml, 194.62 mmol) was added at 0°-5° C. and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of a 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride and the combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 21.22 g (87.2%) of N-(carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)-sarcosine methyl ester (Formula XI: R=CH3 ; R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) which was purified by silica column chromatography (20% ethyl acetate in hexane) to afford an oil.

Workup

  1. customat 0°-5° C
  2. additionwas added at 0°-5° C.
  3. stirringthe resulting mixture was stirred overnight
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with methylene chloride
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ca558b3001d4840a432536d60e832e5
Source dataset
uspto-grants-1996_04
Patent number
US05512576

Reaction notes

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