Triethylamine → Benzyl [2-(2-hydroxybutylcarbamoyl)ethyl]carbamate

HRID 2110922Notes

Reaction equation

HRID 2110922 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:34][CH2:35][CH:36]([OH:39])[CH2:37][CH3:38]>ClCCl>[OH:39][CH:36]([CH2:37][CH3:38])[CH2:35][NH:34][C:14]([CH2:13][CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 261071-Amino-2-butanolHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 57637120Benzyl [2-(2-hydroxybutylcarbamoyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

23.20 g (103.93 mmol) 3-benzyloxycarbonylamino-propionic acid, 14.10 g (104.35 mmol) 1-hydroxybenzotriazole, 18.80 ml (135.07 mmol) triethylamine and 21.00 g (135.27 mmol) (ethyl-3-(3-dimethylamino)-propylcarbodiimide hydrochloride (EDAC) are placed in 150 ml dichloromethane, cooled to 0° C. and stirred for 0.75 hours at this temperature. Then 10.50 g (114.26 mmol) 1-amino-2-butanol are added, and the mixture is stirred for 2.5 hours at 0°-5° C. The reaction mixture is extracted with water and 1 molar sodium carbonate solution, the organic phase is dried and evaporated to dryness. The residue is extracted again with dichloromethane and sodium carbonate solution.

Workup

  1. stirringthe mixture is stirred for 2.5 hours at 0°-5° C
  2. extractionThe reaction mixture is extracted with water and 1 molar sodium carbonate solution
  3. customthe organic phase is dried
  4. customevaporated to dryness
  5. extractionThe residue is extracted again with dichloromethane and sodium carbonate solution

Sources & evidence

ORD record
ord-11580a2f00ea462593b51f06e4b915e3
Source dataset
uspto-grants-2009_04
Patent number
US07517995B2

Reaction notes

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