Benzyl Alcohol → 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

HRID 2396768Notes

Reaction equation

HRID 2396768 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:25])[CH:20]([CH:22](C)[CH3:23])[NH2:21].Cl.[Cl-].[Na+].[CH2:29](Cl)Cl>C(N(CC)CC)C>[CH3:17][O:18][C:19](=[O:25])[CH:20]([NH: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])[CH2:22][CH2:23][CH3:29]

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6344Dichloromethane2×HCID 70918Chlorosulfonyl isocyanateHCID 12498813Valine, methyl ester, hydrochloride (1:1)

Product 1

HCID 542695212-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 7.36 ml (84.9 mmol) of chlorosulfonyl isocyanate in 150 ml of methylene chloride was added benzyl alcohol (8.82 ml, 84.7 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 15.62 g (93.25 mmol) of DL-valine methyl ester hydrochloride in methylene chloride containing triethylamine (36 67 ml) 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 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried, and concentrated in vacuo to yield 30 g of N-(carbobenzyloxyaminosulfonyl)-DL-valine methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 =isopropyl; R3 =H) as a solid.

Workup

  1. additionwas added at 0°-5° C.
  2. stirringthe resulting mixture was stirred overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride (2×200 ml)
  5. washthe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7371b0133c85454f933be72666c64aa7
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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