Trifluoroacetic acid → HCID 86727093, compound

HRID 1502096Notes

Reaction equation

HRID 1502096 reaction equation
[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@H:10]2[O:15][CH2:14][C@H:13]3[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][N:12]3[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[F:9][C:8]1[C:3]([C:1]#[N:2])=[C:4]([CH3:27])[C:5]([C@H:10]2[O:15][CH2:14][C@H:13]3[CH2:16][NH:17][CH2:18][CH2:19][N:12]3[CH2:11]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71273527(3R,9aR)-tert-Butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Product 1

HCID 86727093HCID 86727093, compound

Procedure

(3R,9aR)-tert-Butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1.09 g, 2.90 mmol) was stirred in trifluoroacetic acid (10 mL) for 1 h then concentrated and azeotroped with dichloroethane (3×) to yield the title compound. LC-MS (IE, m/z): 276 [M+1]+; 1H-NMR (500 MHz, DMSO) δ ppm 7.989 (t, J=6.4 Hz, 1H), 7.416 (t, J=8.85 Hz, 1H), 4.959 (dd, J=7.75, 2.35 Hz, 1H), 3.855 (d, J=11.9 Hz, 1H), 3.755 (b, 1H), 3.236-3.54 (m, 8H), 3.066 (d, J=11.5 Hz, 1H), 2.50 (s, 3H).

Workup

  1. concentrationthen concentrated
  2. customazeotroped with dichloroethane (3×)

Sources & evidence

ORD record
ord-da19b1e111604ad2acd3f20ac95f38a0
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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