Trimethylsilyl isocyanate → HCID 49870572, compound

HRID 333900Notes

Reaction equation

[NH2:1][C:2]([CH3:32])([CH3:31])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([N:13]2[CH2:18][CH2:17][C@:16]([CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:15][C:14]2=[O:30])[CH3:12])=[CH:7][CH:6]=1.C[Si]([N:37]=[C:38]=[O:39])(C)C>>[OH:29][C:26]([CH3:27])([CH3:28])[CH2:25][C@@:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:15][C:14](=[O:30])[N:13]([C@H:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]#[C:3][C:2]([NH:1][C:38]([NH2:37])=[O:39])([CH3:31])[CH3:32])=[CH:6][CH:7]=2)[CH3:12])[CH2:18][CH2:17]1

Participants

Reactant 2

HCID 70696Trimethylsilyl isocyanate

HCID 49870322HCID 49870322, compound

Product 1

HCID 49870572HCID 49870572, compound

Procedure

The title compound was prepared following a procedure analogous to that described in Example 15 using (S)-3-((S)-1-(4-(3-amino-3-methylbut-1-ynyl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one and trimethylsilyl isocyanate. LC-MS Method 1 tR=1.43 min, m/z=463; 1H NMR (CDCl3) 1.12 (s, 3H), 1.18 (s, 3H), 1.47 (d, 3H), 1.67 (s, 6H), 2.10-2.30 (4H), 2.38 (m, 1H), 2.77 (m, 1H), 5.58 (q, 1H), 6.78 (d, 1H), 7.08 (d, 1H), 7.30-7.40 (5H).

Sources & evidence

ORD record: ord-29f1b66b6bed409fbeb8f15536260369
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883778B2

Reaction notes

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