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

HRID 2247404Notes

Reaction equation

HRID 2247404 reaction equation
[NH:1]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=O.CCN=C=NCCCN(C)C.Cl.[OH:29][C:30]1[C:38]2[N:37]=NNC=2C=[CH:32][CH:31]=1.C(N(CC)CC)C.NCC(O)CC>C(Cl)Cl.O>[CH2:10]([O:9][C:7](=[O:8])[NH:1][CH2:2][CH2:3][C:4](=[O:6])[NH:37][CH2:38][CH:30]([OH:29])[CH2:31][CH3:32])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 261071-Amino-2-butanolHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture comprising Z-Beta-Ala-OH (9.0 g, 40.3 mmol), EDCI.HCl (10.0 g, 52.4 mmol), hyrdoxybenzotriazole (5.45 g, 40.3 mmol), triethylamine (7.3 ml, 52.4 mmol) in DCM (150 ml) is stirred at 0° C. for 30 minutes. 1-Amino-2-butanol (4.2 ml, 44.3 mmol) is added in one portion and stirring is continued for 1 hour. The reaction mixture is diluted with water (150 ml) and extracted with dichloromethane (2×150 ml) The organic layers are combined, dried over MgSO4, filtered and concentrated in vacuo to yield a crude white solid. The product is purified by chromatography on silica eluting with ethanol-ethyl acetate (1:10) to give the titled compound.

Workup

  1. extractionextracted with dichloromethane (2×150 ml) The organic layers
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield a crude white solid
  6. customThe product is purified by chromatography on silica eluting with ethanol-ethyl acetate (1:10)

Sources & evidence

ORD record
ord-d4c14ba21dcc4bbdb1346e89c015a8e5
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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