Tetrabutylammonium Fluoride → HCID 145857615, compound

HRID 723206Notes

Reaction equation

HRID 723206 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[NH:55])[C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([NH:33]C(OCC[Si](C)(C)C)=O)=[CH:28][C:27]=3[NH:43][C:44](=[O:54])[NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][C:51]([OH:53])=[O:52])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:33][C:29]1[CH:30]=[C:31]([CH3:32])[C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([C:12]3[CH:11]=[C:10]([C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[NH:55])[S:14][C:13]=3[S:15][CH3:16])(=[O:18])=[O:19])[CH:21]=2)=[C:27]([NH:43][C:44](=[O:54])[NH:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][C:51]([OH:53])=[O:52])[CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 145857622HCID 145857622, compound

Product 1

HCID 145857615HCID 145857615, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 6-{3-[3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-biphenyl-2-yl]-ureido}-hexanoic acid ((Example 259: step b) 0.422 g, 0.506 mmol) in dry THF (20 mL) was treated with tetrabutylammonium fluoride (1 M in hexanes, 3.39 mL, 3.39 mmol) and stirred at 40° C. 4 h. Solvents were evaporated in vacuo. The residue was taken up in CH2Cl2 and washed with water (4×50 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. Silica gel chromatography (4% MeOH in CH2Cl2) afforded the product 6-(3-{4-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-hexanoic acid (0.200 g, 57%) as an off-white solid. The material was combined with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (0.252 g, 0.870 mmol) and acetic acid (0.5 mL) in MeOH (10 mL) and was stirred at 40° C. 2 h. The solvent was removed in vacuo. Silica gel chromatography (4% MeOH in CH2Cl2 then 10% MeOH in CH2Cl2) afforded the title compound (0.215 g, 80%) as a white solid. 1H-NMR (CD3OD): δ 8.22 (s, 1H), 8.06 (m, 1H), 7.89 (m, 1H), 7.72 (m, 1H), 7.69 (m, 1H), 7.53 (m, 1H), 7.32 (m, 1H), 3.01 (m, 2H), 2.66 (s, 3H), 2.27 (t, 2H, 7.4 Hz), 1.97 (s, 3H), 1.57 (m, 2H), 1.54 (s, 18H), 1.51 (s, 9H), 1.37 (m, 2H), 1.27 (m, 2H).

Workup

  1. custom4 h
  2. customSolvents were evaporated in vacuo
  3. washwashed with water (4×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a036c0f4d6746a8b42596b5e71f68f2
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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