Isopropyl Acetate → HCID 58109454, compound

HRID 1046218Notes

Reaction equation

[OH:1][C:2]([CH3:36])([CH3:35])[CH2:3][C@@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH2:12]C)[CH2:6][CH2:5]1.Br[C:38]1[S:39][C:40]([C:43]([N:45]([CH3:47])[CH3:46])=[O:44])=[CH:41][N:42]=1.C(OC(C)C)(=O)C>>[OH:1][C:2]([CH3:35])([CH3:36])[CH2:3][C@@:4]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:38]3[S:39][C:40]([C:43]([N:45]([CH3:47])[CH3:46])=[O:44])=[CH:41][N:42]=3)=[CH:18][CH:19]=2)[CH3:12])[CH2:6][CH2:5]1

Participants

Reactant 3

HCID 7915Isopropyl Acetate

HCID 2048236887807-88-3

HCID 66600802(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)-1,3-oxazinan-2-one

Product 1

HCID 58109454HCID 58109454, compound

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propyl)-1,3-oxazinan-2-one and 2-bromo-N,N-dimethylthiazole-5-carboxamide following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=1.215 min, m/z=450.1; 1H NMR (CD3OD) 0.92 (s, 3H), 1.22 (s, 3H), 1.53 (d, 3H), 2.11 (s, 2H), 2.19-2.28 (m, 1H), 2.40-2.58 (m, 2H), 3.00-3.31 (m, 4H), 5.56 (m, 1H), 7.02 (d, 2H), 7.26-7.39 (m, 5H), 7.69 (d, 2H), 8.08 (s, 1H). The compound was dissolved in refluxing isopropyl acetate and allowed to cool slowly to rt to afford a solid with mp 110-111.5° C.

Workup

dissolutionThe compound was dissolved
customto afford a solid with mp 110-111.5° C.

Sources & evidence

ORD record: ord-13eb96361f694c5d8ace55a7d4072905
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569292B2

Reaction notes

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