Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate → HCID 72950421, compound

HRID 709116Notes

Reaction equation

HRID 709116 reaction equation
[F:1][C:2]1([F:22])[CH2:6][C@H:5]([CH:7]=O)[N:4]([CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:3]1=[O:21].COP([CH2:29][C:30](=[O:38])[CH:31]([CH3:37])[CH2:32][C:33]#[C:34][CH2:35][CH3:36])(=O)OC>>[F:1][C:2]1([F:22])[CH2:6][C@H:5](/[CH:7]=[CH:29]/[CH:30]([OH:38])[CH:31]([CH3:37])[CH2:32][C:33]#[C:34][CH2:35][CH3:36])[N:4]([CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[C:3]1=[O:21]

Participants

3

Reactant 2

HCID 13269867Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonateHCID 90054501(R)-methyl 4-(2-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)ethyl)benzoate

Product 1

HCID 72950421HCID 72950421, compound

Procedure

Methyl 4-(2-((5R)-3,3-difluoro-5-((E)-3-hydroxy-4-methylnon-1-en-6-yn-1-yl)-2-oxopyrrolidin-1-yl)ethyl)benzoate was prepared by the method described in Example 1, Steps A and B, except that (R)-methyl 4-(2-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl)ethyl)benzoate (13b) was used instead of (R)-methyl 7-(3,3-difluoro-5-formyl-2-oxopyrrolidin-1-yl) heptanoate (13a) and (±)-dimethyl(3-methyl-2-oxooct-5-yn-1-yl)phosphonate (15bb(i)/15bc(i)) was used instead of (±)-dimethyl(3-methyl-2-oxohept-5-yn-1-yl)phosphonate (15ab(i)/15ac(i)) in Step A.

Sources & evidence

ORD record
ord-23f5076d065946589b0c3d0459162758
Source dataset
uspto-grants-2015_11
Patent number
US09180116B2

Reaction notes

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