Potassium Carbonate → HCID 10099742, compound

HRID 1372173Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][S:22]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=3)[CH:26]=2)(=[O:24])=[O:23])[C:16]1=[O:36].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40].C(=O)([O-])[O-].[K+].[K+]>>[CH3:42][O:41][C:39](=[O:40])[CH2:38][N:21]([S:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=2)[CH:26]=1)(=[O:23])=[O:24])[CH:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:3]2[CH:2]=[CH:7][C:6]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:5][CH:4]=2)[C:16]1=[O:36]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 60984Methyl bromoacetate

HCID 10098361HCID 10098361, compound

Product 1

HCID 10099742HCID 10099742, compound

Procedure

The compound of Example 2 was treated with methyl bromoacetate in the presence of potassium carbonate using the procedure described for the preparation of compound 9, Part A. Purification by flash chromatography provided the title compound. MS(ESI+) (M+H)+. 1HNMR (CDCl3) δ 8.48 (s, 1H); 7.85 (m, 4H); 7.53 (m, 2H); 7.37 (m, 3H); 7.27 (m, 2H); 6.85 (m, 1H); 6.45 (m, 1H); 4.60 (m, 1H); 4.30 (m, 1H); 3.80 (m, 1H); 3.74 (m, 3H); 3.60 (m, 1H); 3.40 (m, 1H); 2.55 (m, 1H); 2.15 (m, 3H) ppm. MS m/z 580.0 (M+H)+. HRMS calcd for C29H27N3O6SCl: 580.1309. Found: 580.1310.

Workup

customPurification by flash chromatography

Sources & evidence

ORD record: ord-2fd7e6969b834006b9ad0ffbe4a56bc2
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157470B2

Reaction notes

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