Triethylamine → HCID 66875137, compound

HRID 1799663Notes

Reaction equation

HRID 1799663 reaction equation
[F:1][C:2]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]=[C:13]=[O:14].Cl.Cl.[CH2:22]([O:29][C:30](=[O:38])[CH2:31][C@@H:32]([NH2:37])[CH2:33][N:34]([CH3:36])[CH3:35])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl>[CH2:22]([O:29][C:30](=[O:38])[CH2:31][C@@H:32]([NH:37][C:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:2]=1[F:1])=[O:14])[CH2:33][N:34]([CH3:35])[CH3:36])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 86635497HCID 86635497, compound

Product 1

HCID 66875137HCID 66875137, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of [6-(2,3-difluoro-benzyloxy)-hexyl]-isocyanate (224 mg, 0.83 mmol) in dichloromethane (1 mL) was added at 0° C. to a suspension of (R)-3-amino-4-dimethylamino butyric acid benzyl ester dihydrochloride (255 mg, 0.83 mmol) in dichloromethane (4 mL), then a solution of triethylamine (167 mg, 1.65 mmol) in dichloromethane (1 mL) was added dropwise over 25 min. The reaction mixture was kept at <5° C. for 1 h, then allowed to reach room temperature over 1 h. Insoluble material was removed by filtration and the filtrate evaporated. The residue was purified by preparative HPLC to afford (R)-3-{3-[6-(2,3-difluoro-benzyloxy)-hexyl]-ureido}-4-dimethylamino-butyric acid benzyl ester (56 mg, 13%) as a colorless oil.

Workup

  1. waitto reach room temperature over 1 h
  2. customInsoluble material was removed by filtration
  3. customthe filtrate evaporated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1a3983961e6e4f839868f74fa9064a1e
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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