Triethylamine → HCID 131726535, compound

HRID 1296284Notes

Reaction equation

HRID 1296284 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]([CH3:20])([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[NH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@:9]([CH3:20])([C:17]([NH:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11140456(R)-2-((tert-Butoxycarbonyl)amino)-2-methyl-3-phenylpropanoic acid

Product 1

HCID 131726535HCID 131726535, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of (R)-N-(tert-butyloxycarbonyl)-α-methylphenylalanine (0.72 g, 2.6 mmol) in dry CH2Cl2 (16 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.69 g, 4.4 mmol) and 1-hydroxybenzotriazole hydrate (0.39 g, 2.9 mmol). The reaction was stirred at ambient temperature for 30 min and then glycine, ethyl ester hydrochloride (0.62 g, 5.2 mmol) and triethylamine (0.85 ml, 5.7 mmol) were added. After stirring at ambient temperature for 3 h, the reaction was transferred to a separatory funnel with CH2Cl2. Extraction with CH2Cl2 and washing of the organic layer with water, saturated NaHCO3, and brine and drying with MgSO4 afforded 0.94 g of crude product after evaporation of the solvent. Purification by flash chromatography (SiO2, 0.2 to 10% MeOH in CH2Cl2) afforded pure product (0.87 g, 93% yield). MS (ESI) 365 (M+H).

Workup

  1. stirringAfter stirring at ambient temperature for 3 h
  2. extractionExtraction with CH2Cl2
  3. washwashing of the organic layer with water, saturated NaHCO3, and brine
  4. dry with materialdrying with MgSO4
  5. customafforded 0.94 g of crude product
  6. customafter evaporation of the solvent
  7. customPurification by flash chromatography (SiO2, 0.2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2bc5027173094dc7a42740890bb05f58
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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