Chlorosulfonic acid → HCID 53879222, compound

HRID 1459007Notes

Reaction equation

HRID 1459007 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].Cl.[C:7]([C:9]1[CH:34]=[CH:33][C:12]([CH2:13][NH:14][C:15](=[O:32])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:31])[C@@H:22]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH2:23])=[CH:11][CH:10]=1)#[N:8].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:15](=[O:32])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:31])[C@@H:22]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:23][S:2]([OH:5])(=[O:4])=[O:3])=[CH:33][CH:34]=1)#[N:8]

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acidHCID 81531DiisopropylethylamineHCID 70066102HCID 70066102, compound

Product 1

HCID 53879222HCID 53879222, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.58 g (0.33 ml, 5 mmol) of chlorosulfonic acid in 10 ml of DCM was slowly added dropwise at 20° C. with cooling to a solution of 1.8 g (4.36 mmol) of D-phenylalanylproline (p-cyanobenzyl)amide hydrochloride and 1.68 g (13.0 mmol) of diisopropylethylamine in 20 ml of DCM. After stirring at room temperature for 30 min, the mixture was diluted to 100 ml with DCM and extracted initially with 2M HCl and then twice with 10 ml of water, and the organic phase was dried over magnesium sulfate and evaporated in a rotary evaporator. 2.0 g of N-hydroxysulfonyl-D-phenylalanylproline (p-cyanobenzyl)amide were obtained as crude product which was used for the next reaction without further purification.

Workup

  1. extractionextracted initially with 2M HCl
  2. dry with materialtwice with 10 ml of water, and the organic phase was dried over magnesium sulfate
  3. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-524ee16ab838404b8c055da15f1c84ae
Source dataset
uspto-grants-1998_12
Patent number
US05852051

Reaction notes

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