Benzenesulfonyl chloride → HCID 70238143, compound

HRID 651797Notes

Reaction equation

[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:15][C:16]([C@H:18]([C@@H:28]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:29]([NH:31][N:32]1[C:36](=[O:37])[C:35]2([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[NH:34][C:33]1=[O:43])=[O:30])[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[C:1]1([S:7]([N:40]2[CH2:41][CH2:42][C:35]3([NH:34][C:33](=[O:43])[N:32]([NH:31][C:29](=[O:30])[C@@H:28]([C@@H:18]([C:16]([O:15][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:17])[CH2:19][CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:44][CH:45]([CH3:46])[CH3:47])[C:36]3=[O:37])[CH2:38][CH2:39]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 70203736HCID 70203736, compound

Product 1

HCID 70238143HCID 70238143, compound

Procedure

In a manner analogous to that described in Example 26, part (i) but using benzenesulphonyl chloride in place of methanesulphonyl chloride from 0.83 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methyl-N-[2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]valeramide there was obtained 0.889 g of N-[8-(benzenesulphonyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-3-yl]-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleramide in the form of a white solid.

Sources & evidence

ORD record: ord-b479abb8c18b4d8991fd488b02f3f282
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281363B1

Reaction notes

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