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

HRID 743448Notes

Reaction equation

HRID 743448 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]1([CH2:14][OH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:17][O:18][C:19](=[O:26])[C:20]([CH2:23][CH2:24][CH3:25])(C)[NH2:21].C(N(CC)CC)C.Cl.[Cl-].[Na+]>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:26])[CH:20]([NH:21][S:2]([NH:5][C:6]([O:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])(=[O:4])=[O:3])[CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 42950514Methyl 2-amino-2-methylpentanoate hydrochloride

Product 1

HCID 542695212-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 15.4 9 ml (0. 178 mol) of chlorosulfonyl isocyanate in methylene chloride was added phenylmethanol (18.5 ml, 0.178 mol) at 0°-5° C. After stirring the above cold solution at this temperature, a solution of 34.9 g (0.192 mol) of 2-propyl-DL-alanine methyl ester hydrochloride in 350 ml of methylene chloride containing triethylamine (73.86 ml, 0.532 mol) was added, and the resulting mixture was stirred for 17 hours allowing the mixture to warm to room temperature. To the reaction mixture was added 500 ml of 10% aq. HCl solution saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×100 ml) and the combined organic layer was dried over magnesium sulfate, concentrated in vacuo, and the residual brown oil was purified by flash chromatography (30% ethyl acetate in hexane) followed by crystallization from ether/hexane to afford 22.35 g (35%) of N-(carbobenzyloxyaminosulfonyl)-2-propyl-DL-alanine methyl ester (Formula XIV: R=CH3 ; R1 =propyl; R2 =CH3 ; R3 =H) as a white solid, m.p. 97°-99° C.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred for 17 hours
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride (2×100 ml)
  5. dry with materialthe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customthe residual brown oil was purified by flash chromatography (30% ethyl acetate in hexane)
  8. customfollowed by crystallization from ether/hexane

Sources & evidence

ORD record
ord-f2d0a9952aa844b59a0568acccdac3ea
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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