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

HRID 2396763Notes

Reaction equation

HRID 2396763 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]([NH2:24])[CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.Cl.[Cl-].[Na+]>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:25])[CH:20]([NH:24][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])[CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 6

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 22492254Methyl 2-aminopentanoate hydrochloride

Product 1

HCID 542695212-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid methyl esterYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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°-5° C. After stirring the above solution for 1.5 hours at this temperature, a solution of 15.62 g (93.25 mmol) of 2-amino-pentanoic acid methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (25.54 g, 0.2528 mol) 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/ethyl acetate (4:1, 2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 28.2 g (87.6%) of 2-(N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (Formula XIV: R=CH3, R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 76°-78° C.

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/ethyl acetate (4:1, 2×200 ml)
  5. washthe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6c1643a0f6b447ebb3553566b8b9c96
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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