Methyl chloroformate → HCID 49870575, compound

HRID 333905Notes

Reaction equation

[OH:1][C:2]([CH3:33])([CH3:32])[CH2:3][C@@:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3([OH:25])[CH2:24][NH:23][CH2:22]3)=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.Cl[C:35]([O:37][CH3:38])=[O:36]>>[OH:25][C:21]1([C:20]#[C:19][C:16]2[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]3[CH2:6][CH2:5][C@:4]([CH2:3][C:2]([OH:1])([CH3:32])[CH3:33])([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:9][C:8]3=[O:10])[CH3:12])=[CH:18][CH:17]=2)[CH2:24][N:23]([C:35]([O:37][CH3:38])=[O:36])[CH2:22]1

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 49870574HCID 49870574, compound

Product 1

HCID 49870575HCID 49870575, compound

Procedure

The title compound was prepared from (S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-((3-hydroxyazetidin-3-yl)ethynyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one and methyl chloroformate following a procedure analogous to that described in Example 14. LC-MS Method 1 tR=1.43 min, m/z=507, 449; 1H NMR (CDCl3) 1.12 (s, 3H), 1.19 (s, 3H), 1.52 (d, 3H), 2.10-2.45 (5H), 2.83 (m, 1H), 3.69 (s, 3H), 4.15 (d, 2H), 4.33 (d, 2H), 5.66 (q, 1H), 6.87 (d, 2H), 7.17 (d, 2H), 7.30-7.40 (5H).

Sources & evidence

ORD record: ord-2496dd83fcda4b648babe6f2b1df3ea2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883778B2

Reaction notes

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