5-Bromo-2-furanecarboxylic acid → HCID 59268848, compound

HRID 889070Notes

Reaction equation

HRID 889070 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:13][C:14]([C:16]1S[C:18]([Br:21])=[CH:19][CH:20]=1)=[O:15])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].BrC1[O:28]C(C(O)=O)=CC=1>>[CH2:1]([O:3][C:4](=[O:22])[C@@H:5]([NH:13][C:14]([C:16]1[O:28][C:18]([Br:21])=[CH:19][CH:20]=1)=[O:15])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2]

Participants

3

Reactant 2

HCID 685115-Bromo-2-furanecarboxylic acidHCID 46180058HCID 46180058, compound

Product 1

HCID 59268848HCID 59268848, compoundYield 72%

Procedure

Compound 13 was prepared using the general method described for the preparation of compound 9 and 13, from 12 (1.91 g, 10 mmol) to give 2.71 g (72%) of 13 as yellow oil. 1H NMR (DMSO-d6): δ 1.13-1.19 (m, 6H), 1.88-2.11 (m, 2H), 2.37-2.41 (t, J=7.2 Hz, 2H), 4.00-4.12 (m, 4H), 4.36-4.41 (m, 1H), 6.77-6.78 (d, J=3.6 Hz, 1H), 7.20-7.21 (d, J=3.6 Hz, 1H), 8.72-8.74 (d, J=7.6 Hz, 1H).

Workup

  1. customCompound 13 was prepared

Sources & evidence

ORD record
ord-2ce901396ea34b0d983a47a7af0d0f3f
Source dataset
uspto-grants-2012_08
Patent number
US08252804B2

Reaction notes

Loading…