HCID 58746756, compound → HCID 69597698, compound

HRID 724613Notes

Reaction equation

HRID 724613 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:27][C:28](=[O:49])[C@@H:29]([NH:37][C:38](=[O:48])[CH2:39][C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])=[CH:13][CH:12]=2)[S:6]1(=[O:51])=[O:50])([CH3:4])([CH3:3])[CH3:2]>C(O)C.CO.ClCCl.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:27][C:28](=[O:49])[C@@H:29]([NH:37][C:38](=[O:48])[CH2:39][C:40]3[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=3)[CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:20])=[CH:13][CH:12]=2)[S:6]1(=[O:51])=[O:50])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 1

HCID 58746756HCID 58746756, compound

Product 1

HCID 69597698HCID 69597698, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneCatalystHCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 401-A (50 mg, 0.07 mmol) and 5% Pd/BaSO4 (5 mg, 10 wt %) in ethanol (1.5 mL), methanol (1.0 mL) and dichloromethane (2 drops) was stirred under an atmosphere of hydrogen for 5 h. The reaction mixture was filtered and concentrated to yield the 401-B (48 mg, 96%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.30–7.26 (m, 4H), 7.22–7.16 (m, 4H), 7.00–6.94 (m, 4H), 6.85–6.81 (m, 2H), 6.43 (dd, J=8.3, 4.9 Hz, 1H), 5.90–5.84 (m, 1H), 5.79 (dd, J=8.8, 6.8 Hz, 1H), 4.75 (ddd, J=10.7, 9.3, 2.0 Hz, 1H), 4.61–4.57 (m, 1H), 4.50 (dd, J=12.2, 6.3 Hz, 1H), 3.82 (s, 3H), 3.43–3.35 (m, 2H), 3.22–3.09 (m, 4H), 3.05–3.03 (m, 1H), 3.00–2.90 (m, 1H), 2.90–2.80 (m, 1H), 1.66 (s, 9H), 1.40–1.35 (m, 2H), 1.35–1.23 (m, 2H), 1.23–1.17 (m, 2H), 0.88 (t, J=7.1 Hz, 3H); LCMS found for C39H51N4O7S (M+H)+: m/z=719.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3f00dd90a21048489aca3f3d8156faff
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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