1,2-Dichloroethane → HCID 44599238, compound

HRID 882771Notes

Reaction equation

HRID 882771 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@:9]1([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH:25]1([N:29]2[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@:9]1([C:13]([N:32]1[CH2:33][CH2:34][CH2:35][N:29]([CH:25]2[CH2:26][CH2:27][CH2:28]2)[CH2:30][CH2:31]1)=[O:15])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 450268891-(tert-Butoxycarbonyl)-2-[(3-fluorophenyl)methyl]-D-prolineHCID 69002457HCID 69002457, compound

Product 1

HCID 44599238HCID 44599238, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (2S)-2-(3-fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (97.0 mg, 0.3 mmol), 1-cyclobutyl-[1,4]diazepane hydrochloride (75.0 mg, 0.3 mmol), HOBt (49.0 mg, 0.36 mmol), EDC (69.2 mg, 0.36 mmol) and N-methylmorpholine (98.0 mg, 0.96 mmol) in CH2Cl2 (10 mL) was stirred at rt for 18 h. The reaction mixture was diluted with CH2Cl2, washed successively with 1 N NaOH and water, dried, and concentrated. The residue (210 mg) was purified by FCC to provide the title compound (47.0 mg, 34%). MS (ESI): mass calcd. for C26H38FN3O3, 459.60; m/z found, 460.2 [M+H]+. 1H NMR (CDCl3): 7.25-7.18 (m, 1H), 6.99-6.83 (m, 3H), 3.61-3.48 (m, 2H), 3.37-3.10 (m, 4H), 2.92-2.52 (m, 3H), 2.49-2.25 (m, 2H), 2.23-1.80 (m, 9H), 1.76-1.55 (m, 5H), 1.51-1.48 (m, 9H).

Workup

  1. washwashed successively with 1 N NaOH and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue (210 mg) was purified by FCC

Sources & evidence

ORD record
ord-c800e5e31b18438d8d44bb94300fe431
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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