1,2-Dichloroethane → 2-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 132878Notes

Reaction equation

HRID 132878 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][NH:31][CH2:32]2)=[CH:27][CH:26]=1)([O-:24])=[O:23].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[CH2:10][C:11]([N:31]1[CH2:30][CH2:29][C:28]2[C:33](=[CH:34][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)[CH2:32]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinolineHCID 7021570(3R)-3-(((tert-butoxy)carbonyl)amino)-4-(2-fluorophenyl)butanoic acid

Product 1

HCID 692227422-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline

Procedure

(3R)-3-[(tert-Butoxycarbonyl)amino]4-(2-fluorophenyl)butanoic acid (0.69 g; 2.34 mmol) and 7-nitro-1,2,3,4 tetrahydroisoquinoline (0.50 g; 2.34 mmol) were treated with EDC (0.54 g, 2.8 mmol), HOBt (0.38 g, 2.8 mmol) and N,N-diisopropylethylamine (0.60 g, 4.67 mmol) essentially following the procedure outlined in Example 1, Step A. Purification by flash chromatography (silica gel; 35% ethyl acetate/hexanes as eluant) afforded the title compound. LC/MS: 358.1 (M+1-BOC)

Workup

  1. customPurification by flash chromatography (silica gel; 35% ethyl acetate/hexanes as eluant)

Sources & evidence

ORD record
ord-81457b8ecf6543988f4194de0641e27a
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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