N-(2-Benzyloxy-5-oxotetrahydrofuran-3-yl)-6,10-dioxo-octahydro-9-(3-phenylpropionylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide → 3-(6,10-Dioxo-octahydro-9-(3-phenylpropionylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamido)-4-oxobutanoic acid

HRID 2230425Notes

Reaction equation

HRID 2230425 reaction equation
C([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]2[N:22]3[C:23](=[O:40])[CH:24]([NH:29][C:30](=[O:39])[CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:25][CH2:26][C:27](=[O:28])[N:21]3[CH2:20][CH2:19][CH2:18]2)=[O:16])[CH2:12][C:11](=[O:41])[O:10]1)C1C=CC=CC=1>[Pd].CO>[O:28]=[C:27]1[CH2:26][CH2:25][CH:24]([NH:29][C:30](=[O:39])[CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:23](=[O:40])[N:22]2[CH:17]([C:15]([NH:14][CH:13]([CH:9]=[O:8])[CH2:12][C:11]([OH:41])=[O:10])=[O:16])[CH2:18][CH2:19][CH2:20][N:21]12

Participants

4

Reactant 1

HCID 18465764N-(2-Benzyloxy-5-oxotetrahydrofuran-3-yl)-6,10-dioxo-octahydro-9-(3-phenylpropionylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide

Product 1

HCID 184656923-(6,10-Dioxo-octahydro-9-(3-phenylpropionylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamido)-4-oxobutanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [3S,2R,S, (1S,9S)] N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)-6,10-dioxo-octahydro-9-(3-phenylpropionylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide (46a) (205 mg; 0.364 mmol), 10% palladium on carbon (200 mg) and methanol (20 ml) was stirred under hydrogen at atmospheric pressure for 5 h. The mixture was filtered then concentrated to yeild 154 mg (90%) of a glass: mp. 116-118° C.; [α]D23 −140° (c 0.1, CH3OH); IR (KBr) 3323 (br), 1783, 1731, 1658, 1539, 1455, 1425; 1H NMR (CD3OD) δ7.21 (5H, m), 5.17 (1H, m), 4.73 (1H, m), 4.50 (2H, m), 4.23 (1H, m), 3.38 (1H, m), 3.06 (1H, m), 2.91 (2H, m), 2.73-2.18 (6H, m) and 2.01-1.59 (5H, m). Anal. Calcd for C23H27N4O7+H2O: C, 56.32; H, 6.16; N, 11.42. Found: C, 56.29; H, 6.11; N, 11.25. MS(FAB, m/z) 473 (M++1), 176, 149, 105, 91.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthen concentrated to yeild 154 mg (90%) of a glass

Sources & evidence

ORD record
ord-a445e3c60e3f420aab097e206b452fdf
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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