Pivalic acid → HCID 58109415, compound

HRID 2037832Notes

Reaction equation

[NH2:1][C:2]([CH3:27])([CH3:26])[CH2:3][C@@:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[C:28](O)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([NH:1][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:26])[CH3:27])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 6417Pivalic acid

HCID 59635772HCID 59635772, compound

Product 1

HCID 58109415HCID 58109415, compound

Procedure

The title compound was prepared (S)-6-(2-amino-2-methylpropyl)-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one following a procedure analogous to that described in Example 688 using pivalic acid. LC-MS Method 1 tR=2.05 min, m/z=515; 1H NMR (CDCl3) 7.36-7.27 (5H, m), 7.22 (2H, d, J=8.5 Hz), 6.79 (2H, d, J=8.2 Hz), 6.20 (1H, s), 5.58 (1H, q, J=7.0 Hz), 2.79 (1H, m), 2.44 (1H, d, J=15.5 Hz), 2.37 (1H, d, J=15.2 Hz), 2.24-2.06 (3H, m), 1.47 (3H, d, J=7.03 Hz), 1.37 (3H, s) 1.10 (9H, s), 1.05 (3H, s).

Sources & evidence

ORD record: ord-ce5856b4b577432cbc90ccdd52d2de75
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

Loading…