tert-Butyl bromoacetate → HCID 60139781, compound

HRID 270513Notes

Reaction equation

HRID 270513 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[NH2:10][CH2:11][CH2:12][CH2:13][C@:14]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:18]([C:19](=[O:24])[C@@H:20]([O:22]C)[CH3:21])[N:17]=[C:16]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[S:15]1>>[NH2:10][CH2:11][CH2:12][CH2:13][C@:14]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:18]([C:19](=[O:24])[C@@H:20]([O:22][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH3:21])[N:17]=[C:16]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[S:15]1

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 60139827HCID 60139827, compound

Product 1

HCID 60139781HCID 60139781, compound

Procedure

Prepared as previously described in Example 71 using tert-butyl 2-bromoacetate in place of methyl iodide. MS ESI (+) m/z 520 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.50 (m, 1H), 7.46 (d, 2H, J=8 Hz), 7.34 (m, 2H), 7.27 (m, 1H), 7.13 (m, 2H), 4.93 (q, 1H, J=6 Hz), 4.18 (d, 1H, J=16 Hz), 3.96 (d, 1H, J=16 Hz), 3.30 (m, 1H), 2.96 (m, 2H), 2.45 (m, 1H), 2.01 (m, 1H), 1.63 (m, 1H), 1.50 (d, 3H, J=6 Hz), 1.46 (s, 9H). Stereochemistry was assigned by inference from (S)-1-((S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a48aef5c821f48ad9e22b91c41026a15
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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