Trifluoroacetic acid methylene chloride → 6-{3-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-2-methyl-biphenyl-4-yl]-ureido}-hexanoic acid ethyl ester trifluoroacetate

HRID 2216218Notes

Reaction equation

HRID 2216218 reaction equation
[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([C:29]3[CH:33]=[C:32]([C:34]([NH:36]C(OC(C)(C)C)=O)=[NH:35])[S:31][C:30]=3[S:44][CH3:45])(=[O:28])=[O:27])[CH:21]=2)=[C:16]([CH3:46])[CH:15]=1)=[O:12])[CH3:2].[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49].C(Cl)Cl>>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[CH2:1]([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([C:29]3[CH:33]=[C:32]([C:34](=[NH:35])[NH2:36])[S:31][C:30]=3[S:44][CH3:45])(=[O:27])=[O:28])[CH:21]=2)=[C:16]([CH3:46])[CH:15]=1)=[O:12])[CH3:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 145857680ethyl 6-[[3-methyl-4-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]hexanoate

Product 1

HCID 695864936-{3-[3'-(5-Carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-2-methyl-biphenyl-4-yl]-ureido}-hexanoic acid ethyl ester trifluoroacetate

Procedure

Following the procedure in Example 1: step d, 6-(3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-2-methyl-biphenyl-4-yl}-ureido)-hexanoic acid ethyl ester ((Example 311: step a) 12 mg) was treated with 1:1 TFA/DCM. Purification by HPLC yielded the product (8.3 mg) as a white solid. 1H-NMR (CD3OD): δ 8.31 (s, 1H), 7.97 (m, 1H), 7.94 (m, 1H), 7.65 (m, 2H), 7.29 (m, 2H), 7.09 (m, 1H), 4.10 (q, 2H, 7.2 Hz), 3.20 (t, 2H, 7.0 Hz), 2.71 (s, 3H), 2.33 (t, 2H, J=7.3 Hz), 2.19 (s, 3H), 1.65 (m, 2H), 1.55 (m, 2H), 1.40 (m, 2H), 1.23 (t, 3H, J=7.2 Hz). ESI-MS (m/z): Calcd. for C28H34N4O5S3 (M+H): 603.2; found: 603.2.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-ae7f40c5a9fa49c1a740092a9c2cbe0a
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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