Trifluoroacetic acid → HCID 11541643, compound

HRID 2301533Notes

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][CH2:25][NH:26]C(OC(C)(C)C)=O)(=[O:21])=[O:20])[C:13]=1[OH:34])=[O:10].[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[NH2:26][CH2:25][CH2:24][CH2:23][NH:22][S:19]([C:14]1[C:13]([OH:34])=[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:21])=[O:20]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11512586HCID 11512586, compound

Product 1

HCID 11541643HCID 11541643, compoundYield 75%

Procedure

Following the general procedure for Boc deprotection outlined in example 36, N-(2-bromophenyl)-N′[3-[N″-[3-(t-butoxycarbonylamino)propyl]aminosulfonyl)-4-chloro-2- hydroxyphenyl] urea (21 mg, 0.036 mmol) was stirred in 1 mL of trifluoroacetic acid to from the desired product (16 mg, 75%). 1H NMR (MeOD-d4): δ 8.28 (d, 1H), 7.80 (d, 1H), 7.59 (d, 1H), 7.33 (t, 1H), 7.07 (d, 1H), 7.02 (d, 1H) 3.05 (m, 4H) 1.87 (m, 2H).

Sources & evidence

ORD record: ord-f17b3d729b7c422083db5c11a848ae6e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500863B1

Reaction notes

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