2,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamide → HCID 73603574, compound

HRID 1500306Notes

Reaction equation

HRID 1500306 reaction equation
[Cl:1][CH:2]([Cl:21])[C:3]([NH:5][C@H:6]([CH2:19][F:20])[C@H:7]([OH:18])[C:8]1[CH:13]=[CH:12][C:11]([Sn](C)(C)C)=[CH:10][CH:9]=1)=[O:4].Br[C:23]1[CH:24]=[CH:25][C:26]([CH:29]([CH3:32])[C:30]#[N:31])=[N:27][CH:28]=1>>[Cl:1][CH:2]([Cl:21])[C:3]([NH:5][C@H:6]([CH2:19][F:20])[C@@H:7]([C:8]1[CH:13]=[CH:12][C:11]([C:23]2[CH:28]=[N:27][C:26]([CH:29]([C:30]#[N:31])[CH3:32])=[CH:25][CH:24]=2)=[CH:10][CH:9]=1)[OH:18])=[O:4]

Participants

3

Reactant 2

HCID 866953832,2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-trimethylstannanyl-phenyl)-ethyl]-acetamideHCID 86713193HCID 86713193, compound

Product 1

HCID 73603574HCID 73603574, compound

Procedure

Following the general procedure of step 3, Example 4 and using the product of step 2, Example 4 and making non-critical variations but using the product of step 1, Example 23, the title compound is obtained (85 mg): 1H NMR (300 MHz, DMSO-d6) δ 1.61 (d, 3H), 4.25 (m, 1.5H), 4.40-4.60 (m, 2H), 4.70 (m, 0.5H), 4.91 (m, 1H), 5.99 (d, 1H), 6.53 (s, 1H), 7.48 (d, 2H), 7.55 (d, 1H), 7.70 (d, 2H), 8.13 (dd, 1H), 8.62 (bd, 1H), 8.89 (m, 1H). MS (ESI+) m/z 410 [M+H].

Sources & evidence

ORD record
ord-700cf82cbb8d4c909857de29ec2f761f
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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