Triethylamine → HCID 57131393, compound

HRID 274235Notes

Reaction equation

HRID 274235 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10]1([C:15](O)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:27]([O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH2:34][S:35][CH3:36])[NH2:32])[CH3:28].C(N(CC)CC)C.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:27]([O:29][C:30](=[O:37])[C@H:31]([CH2:33][CH2:34][S:35][CH3:36])[NH:32][C:15]([C:10]1([CH2:9][CH:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:16])[CH3:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3083785Ethyl L-methionate hydrochlorideHCID 229034441-(2-t-Butoxycarbonyl-4-phenylbutyl)cyclopentanecarboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 57131393HCID 57131393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine the product of Step 1 (1.50 g, 4.33 mmol) with (S)-methionine ethyl ester hydrochloride (0.92 g, 4.33 mmol), triethylamine (0.65 g, 6.5 mmol), hydroxybenzotriazole (HOBT) (0.66 g, 4.33 mmol), and 1-(3-dimethylaminopropyl)- 3-ethylcarbodiimide hydrochloride (DEC) (0.91 g, 4.8 mmol) in 25 ml dimethylformamide (DMF). Stir 18 h., partition between EtOAc-H20, wash with 1N NaHCO3 and concentrate. Chromatograph the resultant residue on silica, eluting with hexane-ether 1:1 to obtain an oil, [α]D26 =-17.4° (EtOH).

Workup

  1. custompartition between EtOAc-H20
  2. washwash with 1N NaHCO3
  3. concentrationconcentrate
  4. washChromatograph the resultant residue on silica, eluting with hexane-ether 1:1
  5. customto obtain an oil, [α]D26 =-17.4° (EtOH)

Sources & evidence

ORD record
ord-f9b351a24c294e63b4e264e1b48edf85
Source dataset
uspto-grants-1995_02
Patent number
US05389610

Reaction notes

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