2-Thiopheneboronic acid → HCID 58109428, compound

HRID 2037501Notes

Reaction equation

HRID 2037501 reaction equation
[CH2:1]([C@@:4]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].S1C=CC=C1B(O)[OH:36]>>[OH:36][CH2:3][CH2:2][CH2:1][C@@:4]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 66857515HCID 66857515, compound

Product 1

HCID 58109428HCID 58109428, compound

Procedure

The title compound was prepared from (R)-6-allyl-6-phenyl-3-((S)-1-(4-(thiophen-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one and thiophene-2-boronic acid using a procedure analogous to that described in Example 64 followed by a procedure analogous to that described in Example 78. LC-MS Method 2 tR=2.47, min, m/z=422; 1H NMR (CDCl3) 1.49 (d, 3H), 1.84-1.92 (m, 2H), 2.0-2.15 (m, 4H), 2.25 (m, 2H), 2.84 (m, 1H), 3.52 (m, 1H), 4.20 (m, 1H), 5.60 (m, 1H), 6.82 (dd, 2H), 7.0 (m, 1H), 7.15-7.38 (m, 9H).

Sources & evidence

ORD record
ord-78cd3af82a5348f48a6959f314937699
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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