Trifluoroacetic acid → HCID 69824400, compound

HRID 2301537Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([NH:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)(=[O:21])=[O:20])[C:13]=1[OH:33])=[O:10].[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[NH2:25][CH2:24][CH2:23][NH:22][S:19]([C:14]1[C:13]([OH:33])=[C:12]([NH:11][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[O:10])[CH:17]=[CH:16][C:15]=1[Cl:18])(=[O:20])=[O:21]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11664109HCID 11664109, compound

Product 1

HCID 69824400HCID 69824400, compoundYield 34%

Procedure

Following the general procedure for Boc deprotection outlined in example 36, N-(2-bromophenyl)-N′[3-[N″-[2-(tert-butoxycarbonylamino)ethyl]aminosulfonyl]4-chloro-2-hydroxyphenyl] urea (80 mg, 0.14 mmol) was stirred in trifluoroacetic acid to form the desired product (22 mg, 34%). LC-MS 465.0 (M+).

Sources & evidence

ORD record: ord-7e275bdb5c214566aee9c101fbdf4b6c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500863B1

Reaction notes

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