Triethylamine → HCID 57637044, compound

HRID 1804559Notes

Reaction equation

HRID 1804559 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.Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[NH2:46][CH2:47][CH:48]([OH:52])[CH:49]([CH3:51])[CH3:50]>ClCCl>[OH:52][CH:48]([CH:49]([CH3:51])[CH3:50])[CH2:47][NH:46][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

7

Reactant 5

HCID 8471TriethylamineHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223486411-Amino-3-methylbutan-2-olHCID 178418300HCID 178418300, compound

Product 1

HCID 57637044HCID 57637044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

46.00 g (206.07 mmol) 3-benzyloxycarbonylamino-propionic acid, 51.37 g (267.95 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 27.85 g (206.07 mmol) hydroxybenzotriazole (HOBT) and 37.14 ml (267.95 mmol) triethylamine are placed in 700 ml dichloromethane, the mixture is stirred for 0.5 hours at 0°, then 23.70 g (229.73 mmol) 1-amino-3-methyl-butan-2-ol are added. The reaction mixture is stirred for 16 hours at ambient temperature. Then it is extracted with potassium carbonate solution and dichloromethane. The organic phase is washed with 1 molar sodium hydroxide solution, dried and evaporated to dryness. The residue is extracted with diethyl ether, then recrystallised with acetonitrile.

Workup

  1. stirringThe reaction mixture is stirred for 16 hours at ambient temperature
  2. extractionThen it is extracted with potassium carbonate solution and dichloromethane
  3. washThe organic phase is washed with 1 molar sodium hydroxide solution
  4. customdried
  5. customevaporated to dryness
  6. extractionThe residue is extracted with diethyl ether
  7. customrecrystallised with acetonitrile

Sources & evidence

ORD record
ord-8b5331ef80404a6297d837d94f8b4472
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

Loading…