tert-Butanol → HCID 58109510, compound

HRID 2037756Notes

Reaction equation

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

Participants

Reactant 3

HCID 6386tert-Butanol

HCID 22261314Acetonitrile--hydrogen chloride (1/1)

HCID 58109450HCID 58109450, compound

Product 1

HCID 58109510HCID 58109510, compound

Procedure

The title compound was prepared from 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanamide following a procedure analogous to that described in Example 612 using t-butanol as solvent followed by treatment with 2 N aq HCl/CH3CN at rt. LC-MS Method 1 tR=1.41 min, m/z=449, 451 (M+1); 1H NMR (CD3OD) 7.28-7.20 (m, 4H), 7.04 (t, J=8.6 Hz, 2H), 6.96 (d, J=8.2 Hz, 2H), 5.46 (q, J=7.0 Hz, 1H), 2.99-2.94 (m, 1H), 2.34-2.28 (m, 3H), 2.16-2.07 (m, 2H), 1.43 (d, J=7.0 Hz, 3H), 1.13 (s, 3H), 0.90 (s, 3H).

Sources & evidence

ORD record: ord-b22a6bfbaa1d458ea1582b64ff42549f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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