2-Naphthalenesulfonyl chloride → HCID 178427607, compound

HRID 2403997Notes

Reaction equation

HRID 2403997 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:41])[C@@H:15]([NH2:40])[CH2:16][CH2:17][CH2:18][NH:19]/[C:20](/[NH2:39])=[N:21]/[S:22]([C:25]2[C:26]([CH3:38])=[C:27]([CH3:37])[C:28]3[O:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]=3[C:35]=2[CH3:36])(=[O:24])=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46][C:45]=1[S:54](Cl)(=[O:56])=[O:55]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:41])[C@@H:15]([NH:40][S:54]([C:45]2[CH:46]=[CH:47][C:48]3[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:44]=2)(=[O:56])=[O:55])[CH2:16][CH2:17][CH2:18][NH:19]/[C:20](/[NH2:39])=[N:21]/[S:22]([C:25]2[C:26]([CH3:38])=[C:27]([CH3:37])[C:28]3[O:32][C:31]([CH3:33])([CH3:34])[CH2:30][C:29]=3[C:35]=2[CH3:36])(=[O:23])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 1784275624-[(S)-2-Amino-5-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl)-amino)-pentanoyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178427607HCID 178427607, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of compound U (28.0 g, 46.2 mmol) in THF (250 mL) was added aqueous 1N NaOH (171 mL). The reaction mixture was cooled to ˜5° C., a solution of 2-naphthalene sulfonylchloride (26.19 g, 115.6 mmol) in THF (125 mL) was added dropwise. The reaction mixture was stirred at ˜5° C. for 10 min, with stirring continued at room temperature for 2 h. The reaction mixture was diluted with EtOAc (1 L), washed with aqueous 1N NaOH (1 L), water (1 L) and brine (1 L). The organic layer was separated, dried over Na2SO4 and removal of the solvent in vacuo to afford compound V (36.6 g, 46.2 mmol). LC-MS [M+H] 785.5 (C38H52N6O8S2+H, calc: 785.9).

Workup

  1. stirringwith stirring
  2. waitcontinued at room temperature for 2 h
  3. washwashed with aqueous 1N NaOH (1 L), water (1 L) and brine (1 L)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-1a28939ea0fa4bae9dcb76d670b6a0ec
Source dataset
uspto-grants-2014_08
Patent number
US08802681B2

Reaction notes

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