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

HRID 1804552Notes

Reaction equation

HRID 1804552 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)-propylcarbondiimide 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, 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-060b503714504847a07bcf837a32978d
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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