Hydrochloric Acid → N-(BOC-aminoethyl)epsilon-(2-chlorobenzyloxycarbonyl)-lysine allyl ester

HRID 2119763Notes

Reaction equation

HRID 2119763 reaction equation
[CH2:1]([O:4][C:5](=[O:24])[C@H:6]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[O:14])[NH2:12])[NH2:7])[CH:2]=[CH2:3].C([BH3-])#N.[Na+].[C:29]([CH:36]([NH2:39])[CH:37]=O)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].Cl>CO.CCOCC.C(O)(=O)C>[CH2:1]([O:4][C:5](=[O:24])[C@H:6]([CH2:8][CH2:9][CH2:10][CH:11]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])=[O:14])[NH2:12])[NH:7][CH2:37][CH:36]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[NH2:39])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 54347483epsilon-(2-Chlorobenzyloxycarbonyl)-lysine allyl esterHCID 57245992BOC-amino-acetaldehyde

Product 1

HCID 86586571N-(BOC-aminoethyl)epsilon-(2-chlorobenzyloxycarbonyl)-lysine allyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

ε-(2-chlorobenzyloxycarbonyl)-lysine allyl ester (from example 18) was dissolved in methanol (50 mL) and cooled to 0° C. To the resulting solution was added sodium cyanoborohydride (5.9 mmol) followed by acetic acid (0.75 mL). After 5 minutes BOC-amino-acetaldehyde (13.3 mmol) was added and the reaction mixture was stirred for an additional 1 h. The methanol was removed in vacuo and the oil was dissolved in ethyl acetate (40 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated to give a clear colorless oil. This oil was dissolved in dry ether (80 mL), cooled to −20° C., and a molar equivalent of HCl in ether was added slowly. The resulting white solid was collected by filtration and air dried. Precipitation of the air-dried white solid from dry ether gave analytically pure title compound.

Workup

  1. customThe methanol was removed in vacuo
  2. dissolutionthe oil was dissolved in ethyl acetate (40 mL)
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a clear colorless oil
  7. temperaturecooled to −20° C.
  8. filtrationThe resulting white solid was collected by filtration and air
  9. customdried
  10. customPrecipitation of the air-dried white solid from dry ether

Sources & evidence

ORD record
ord-ae64d347f3b54c5fae8c8da70165a3c9
Source dataset
uspto-grants-2004_02
Patent number
US06686442B2

Reaction notes

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