HCID 69338612, compound → HCID 11952815, compound

HRID 1241463Notes

Reaction equation

HRID 1241463 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:16]=2[C:15](=[O:23])[N:14]([C@@H:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH3:25])[C@@H:13]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[C:12]1=[O:40])(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@H:13]2[C:12](=[O:40])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:41])=[O:5])[C:17]3[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:16]=3[C:15](=[O:23])[N:14]2[C@@H:24]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[CH3:25])=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 69338612HCID 69338612, compound

Product 1

HCID 11952815HCID 11952815, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-{(3S)-3-(4-Chloro-phenyl)-4-[(R)-1-(4-chloro-phenyl)-ethyl]-7-iodo-2,5-dioxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl}-pentanoic acid tert-butyl ester (1.0 g, 1.4 mmol) was dissolved in a solution of 20% TFA [10 mL] in dichloromethane at room temperature for 2 hours. The reaction was concentrated and the product was purified by chromatography (hexane: EtOAc 1:1) to give the title compound (0.88 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ 7.75 (d, J=2.3 Hz. 1H), 7.62–7.56 (m, 3H), 7.39 (d, J=8.6 Hz, 2H), 7.00 (d, J=8.6 Hz, 2H), 6.92 (d, J=8.6 Hz, 1H), 6.58–6.56 (m, 2H), 6.21–6.14 (m, 1H), 5.27 (s, 1H), 4.24–4.15 (m, 1H), 3.69–3.61 (m, 1H), 1.80 (t, J=7.2 Hz, 2H), 1.63 (d, J=7.2 Hz, 3H), 1.56–1.21 (m, 4H). Mass spectrum (LCMS, ESI pos.): Calcd for C28H25Cl2IN2O4: 650.02; found 650.8(M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe product was purified by chromatography (hexane: EtOAc 1:1)

Sources & evidence

ORD record
ord-d80d69d7938d4fdd85d5fc5750ef91f8
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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