Trifluoroacetic acid → HCID 88012013, compound

HRID 2301599Notes

Reaction equation

C(OC([NH:8][CH:9]([C:38]([OH:40])=[O:39])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]1[C:19]([OH:37])=[C:20]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=2[Cl:36])=[O:27])[CH:21]=[CH:22][C:23]=1[Cl:24])(=[O:17])=[O:16])=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[NH2:8][CH:9]([C:38]([OH:40])=[O:39])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]1[C:19]([OH:37])=[C:20]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=2[Cl:36])=[O:27])[CH:21]=[CH:22][C:23]=1[Cl:24])(=[O:17])=[O:16]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11643132HCID 11643132, compound

Product 1

HCID 88012013HCID 88012013, compoundYield 74%

Procedure

Following the general procedure for Boc deprotection in example 36, N-[3-[N″-[5-(tert-butoxycarbonylamino)-5-carboxypentyl]aminosulfonyl]-4-chloro-2-hydroxyphenyl]-N′-(2,3-dichlorophenyl) urea (100 mg, 0.16 mmol) was stirred in 1 mL of trifluoroacetic acid to form the desired product (78 mg, 74%). LC-MS (m/z) 541.0 (M+).

Sources & evidence

ORD record: ord-6e4fd5d4139043b1b17c1ab70ff97ed3
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500863B1

Reaction notes

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