Chlorosulfonic acid → HCID 9850567, compound

HRID 1884336Notes

Reaction equation

HRID 1884336 reaction equation
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:2]([C:7]([NH:9][C:10]2[CH:30]=[CH:29][C:13]([C:14]([N:16]3[C:27]4[C:28]5[C:20](=[CH:21][NH:22][C:23]=5[CH:24]=[CH:25][CH:26]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.Cl[S:38]([OH:41])(=[O:40])=[O:39]>C(Cl)Cl>[C:1]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:2]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:16]3[C:27]4[C:28]5[C:20](=[C:21]([S:38]([OH:41])(=[O:40])=[O:39])[NH:22][C:23]=5[CH:24]=[CH:25][CH:26]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:29][CH:30]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 9826033HCID 9826033, compound

Product 1

HCID 9850567HCID 9850567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10 (0.20 g, 0.42 mmol) in CH2Cl2 (100 mL) at about 0° C. was treated with chlorosulfonic acid (0.056 g, 1.1 eq) and stirred for about 2 h. The reaction was Warmed to about rt, stirred for about 18 h and evaporated to a tan powder. The powder was purified by preparative HPLC (MeCN:water, 1:3) to give 18 (tan powder). 1H NMR (DMSO-d6) 2.1 (m, 4 H), 3.0 (m, 1 H), 3.2 (t, J=4, 1 H), 6.1 (m, 1 H), 6.7 (t, J=6, 1 H), 6.9 (d, J=5, 1 H), 7.1 (m, 4 H), 7.3-7.6 (m, 9 H), 10.3 (br. s, 2 H), 11.1 (s, 1 H). MS m/e 552.62 (MH+).

Workup

  1. temperatureThe reaction was Warmed to about rt
  2. stirringstirred for about 18 h
  3. customevaporated to a tan powder
  4. customThe powder was purified by preparative HPLC (MeCN:water, 1:3)

Sources & evidence

ORD record
ord-4f0056a808da4d90aa0b6d7cd87ab088
Source dataset
uspto-grants-2004_07
Patent number
US06765004B1

Reaction notes

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