Ethyl bromoacetate → HCID 137194560, compound

HRID 2110602Notes

Reaction equation

[NH2:1][C:2]1([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([NH:23]C(=O)OC(C)(C)C)=[CH:22][C:16]=3[S:15](=[O:32])(=[O:31])[N:14]=2)[C:3]1=[O:33].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].C([O-])([O-])=O.[K+].[K+]>>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][NH:1][C:2]1([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([NH:23][S:15]([CH3:16])(=[O:32])=[O:31])=[CH:22][C:16]=3[S:15](=[O:31])(=[O:32])[N:14]=2)[C:3]1=[O:33])[CH3:45]

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 11430Potassium Carbonate

HCID 135885150HCID 135885150, compound

Product 1

HCID 137194560HCID 137194560, compound

Procedure

Follow same procedure as Example 18D, treating the product of Example 18C with ethyl bromoacetate (5.7μL, 0.05 mmol) and K2CO3 (6.8 mg, 0.05 mmol). 1H NMR (d6-DMSO) δ 13.81 (s, 1H), 9.98 (s, 1H), 8.16, 8.13 (d, 1H), 7.85, 7.83 (d, 1H), 7.69-7.43 (m, 4H), 7.38, 7.35 (d, 1H), 4.15-4.00 (q, 2H), 3.44, 3.38, 3.23, 3.17 (dd, 1H), 3.02 (s, 3H), 2.32-2.16 (m, 1H), 2.15-2.01 (m, 1H), 1.38-1.21 (m, 2H) 1.21-1.09 (t, 3H), 1.09-0.93 (m, 1H), 0.73-0.62 (q, 6H), 0.55-0.42 (m, 1H); MS (ESI) m/z 605 (M+H+).

Sources & evidence

ORD record: ord-1229113c22414cecb367b7034f2f58a4
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517876B2

Reaction notes

Loading…