HCID 21964606, compound → HCID 69584954, compound

HRID 2212455Notes

Reaction equation

HRID 2212455 reaction equation
[C:1]([CH2:4][O:5][C:6](=[O:20])[C@:7]([NH:18][NH2:19])([CH3:17])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:16])[CH:10]=1)(O)=O.BrCC[CH2:24][C:25]([O:27]CC1C=CC(OC)=CC=1OC)=[O:26]>>[OH:16][C:11]1[CH:10]=[C:9]([CH2:8][C@@:7]([NH:18][NH2:19])([CH3:17])[C:6]([O:5][CH2:4][CH2:1][CH2:24][C:25]([OH:27])=[O:26])=[O:20])[CH:14]=[CH:13][C:12]=1[OH:15]

Participants

3

Reactant 2

HCID 21964606HCID 21964606, compoundHCID 69584869HCID 69584869, compound

Product 1

HCID 69584954HCID 69584954, compoundYield 41%

Procedure

Following the procedure described for preparation of compound 229, and substituting tert-butyl bromomethyl acetate with 2,4-dimethoxybenzyl γ-bromobutyrate, provided the title compound (41% over 2 steps) as a colorless thick liquid. 1H NMR (400 MHz, CD3OD): δ1.45 (3H, s), 1.95 (2H, q), 2.35 (2H, t), 2.86(2H, m), 4.21 (2H, m), 6.46 (1H, dd), 6.56(1H, d), 6.68 (1H, d). MS (ESI) m/z 313.21 (M+H+) and 311.18 (M−H−).

Sources & evidence

ORD record
ord-c92377de55b342d6bd681c9f71a75051
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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