HCID 18396559, compound → HCID 18465745, compound

HRID 2230450Notes

Reaction equation

HRID 2230450 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][C@H:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])[C:5](=[O:14])[N:4]2[C@H:15]([C:19]([OH:21])=O)[CH2:16][CH2:17][CH2:18][N:3]12.C(OC([NH:28][C@H:29]([CH:38]([OH:50])[C:39]1[O:40][C:41]2[C:47]([Cl:48])=[CH:46][C:45]([Cl:49])=[CH:44][C:42]=2[N:43]=1)[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=O)C=C.C(NC1C(=O)N2C(C(NC(C(O)COCC3C(Cl)=CC=CC=3Cl)CC(OC(C)(C)C)=O)=O)CCCN2C(=O)CC1)(=O)C1C=CC=CC=1>>[Cl:49][C:45]1[CH:46]=[C:47]([Cl:48])[C:41]2[O:40][C:39]([CH:38]([OH:50])[CH:29]([NH:28][C:19]([CH:15]3[N:4]4[C:5](=[O:14])[CH:6]([NH:9][S:10]([CH3:13])(=[O:11])=[O:12])[CH2:7][CH2:8][C:2](=[O:1])[N:3]4[CH2:18][CH2:17][CH2:16]3)=[O:21])[CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])=[N:43][C:42]=2[CH:44]=1

Participants

4

Reactant 3

HCID 18396559HCID 18396559, compoundHCID 54324685HCID 54324685, compoundHCID 66756783HCID 66756783, compound

Product 1

HCID 18465745HCID 18465745, compound

Procedure

was prepared from the acid 212b and (3S,4RS) t-butyl N-(allyloxycarbonyl)-3-amino-4-hydroxy-4-(5,7-dichlorobenzoxazol-2-yl)butanoate (204) by an analogous method as that used for compound 215e to afford a mixture of diastereomers (460 mg, 70%) as a glass: IR (film) 3325, 1725, 1664, 1453, 1399, 1373, 1327, 1274, 1256, 1155; 1H NMR (CDCl3) δ7.57 (1H, m), 7.36 (2H, m), 6.06 (1H, t), 5.29 (2H, m), 4.79 (1H, m), 4.47 (1H, m), 3.23 (1H, m), 2.97 and 2.94(3H combined, 2×s), 2.9-2.4 (4H, m), 2.30 (1H, m), 1.96 (4H, m), 1.41 and 1.37 (9H combined, 2×s). MS ES Da/e 660 (M−1)− Cl35 100%, 662 (M−1) Cl37.

Workup

  1. customto afford
  2. additiona mixture of diastereomers (460 mg, 70%) as a glass

Sources & evidence

ORD record
ord-4cabac0b95bf446db8f30733d407b95c
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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