Methanol → HCID 66756912, compound

HRID 1182528Notes

Reaction equation

HRID 1182528 reaction equation
[K+].[Br-].C([C:10]1[N:15]([CH2:16][C:17]([NH:19][CH:20]([C:25](=[O:38])[CH2:26][O:27][C:28](=[O:37])[C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])[CH2:21][C:22]([OH:24])=[O:23])=[O:18])[C:14](=[O:39])[C:13]([NH:40][C:41](=[O:50])CCC2C=CC=CC=2)=[CH:12][CH:11]=1)C1C=CC=CC=1.[CH3:51][OH:52]>>[CH2:51]([O:52][C:41]([NH:40][C:13]1[C:14](=[O:39])[N:15]([CH2:16][C:17]([NH:19][CH:20]([C:25](=[O:38])[CH2:26][O:27][C:28](=[O:37])[C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])[CH2:21][C:22]([OH:24])=[O:23])=[O:18])[CH:10]=[CH:11][CH:12]=1)=[O:50])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 253877Potassium BromideHCID 66756449HCID 66756449, compound

Product 1

HCID 66756912HCID 66756912, compoundYield 78%

Procedure

The ester (56a) (210 mg, 0.356 mmol) in dichloromethane (0.5 ml) was cooled to 0° C. and treated with trifluoroacetic acid (0.5 ml), stirred and warmed to 20° C. over 30 minutes. The solution was evaporated to dryness under reduced pressure, redissolved in dichloromethane and concentrated (x3). The residue was triturated with ethyl acetate and diluted with ether to afford the title compound 162 mg (85%) as a colorless solid: m.p. 165-8° C. (decomposition); [α]D23 −38.8° (c 0.1, CH3OH); IR (KBr) 3332, 3275, 1723, 1658, 1649, 1597, 1581, 1562, 1526, 1432, 1385, 1258, 1218, 1206; 1H NMR (d6-DMSO) δ 8.96 (1H, d, J=7.3), 8.34 (1H, s), 7.85 (1H, dd, J=7.3), 7.58 (3H, m), 7.35 (5H, m), 6.29 (1H, t, J=7.3), 5.26 (2H, m), 5.15 (2H, s), 4.69 (3H, m), 2.75 (2H, m). Anal. Calcd. C27H23N3O9Cl2: C, 53.66; H, 3.84; N, 6.95. Found: C, 53.36; H, 3.90; N, 6.81. M.S. (+FAB); 604 (M++1), 285, 241, 195, 173, 149, 91. N-2-(6-Benzyl-1,2-dihydro-2-oxo-3-(3-phenylpropionyl) amino-1-pyridyl)acetyl-3-amino-5-(2,6-dichloro-benzoyloxy)-4-oxo-pentanoic acid (57b; P), was prepared by the method described for 57a which afforded the title compound (78%) as colorless crystals: m.p. 116-120° C. (decomposition); [α]D26 −41.1° (c 0.1, CH3OH); IR (KBr) 3299, 1739, 1715, 1689, 1666, 1645, 1598, 1563, 1518, 1432, 1209, 1151; 1H NMR (d6-DMSO) δ 9.24 (1H, s), 8.88 (1H, d, J=7.6), 8.18 (1H, d, J=7.7), 7.60 (3H, m), 7.26 (10H, m), 6.06 (1H, d, J=7.7), 5.23 (2H, ABq), 4.69 (3H, m), 3.93 (2H, s), 2.78 (6H, m). Anal. Calcd. for C35H31N3O8Cl2. H2O: C, 59.16; H, 4.68; N, 5.91. Found: C, 59.38; H, 4.53; N, 5.84. M.S. (+FAB); 694, (Cl=35, 37), (M++1); 692 (Cl=35, 35), (M++1).

Sources & evidence

ORD record
ord-5f07282282994ec989c0520f7f71b147
Source dataset
uspto-grants-2007_10
Patent number
US07288624B2

Reaction notes

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