Triethylamine → tert-butyl N-[4-[3-[2-[11-(9H-fluoren-9-ylmethoxycarbonylamino)undecanoylamino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723176Notes

Reaction equation

HRID 723176 reaction equation
S(Cl)(Cl)=O.[CH:5]1[C:17]2[CH:16]([CH2:18][O:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[C:36]([O:40][C:41](=[O:69])[NH:42][C:43]([C:45]1[S:46][C:47]([S:67][CH3:68])=[C:48]([S:50]([C:53]2[CH:54]=[C:55]([C:59]3[C:64]([CH3:65])=[CH:63][CH:62]=[CH:61][C:60]=3[NH2:66])[CH:56]=[CH:57][CH:58]=2)(=[O:52])=[O:51])[CH:49]=1)=[NH:44])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>ClCCl.CN(C=O)C.ClCCl>[CH:14]1[C:15]2[CH:16]([CH2:18][O:19][C:20](=[O:21])[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](=[O:34])[NH:66][C:60]3[CH:61]=[CH:62][CH:63]=[C:64]([CH3:65])[C:59]=3[C:55]3[CH:56]=[CH:57][CH:58]=[C:53]([S:50]([C:48]4[CH:49]=[C:45]([C:43]([NH:42][C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:69])=[NH:44])[S:46][C:47]=4[S:67][CH3:68])(=[O:52])=[O:51])[CH:54]=3)[C:17]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 4393960Fmoc-11-Aun-OHHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857666tert-butyl N-[4-[3-[2-[11-(9H-fluoren-9-ylmethoxycarbonylamino)undecanoylamino]-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 47%

Reagents, catalysts & solvents 2

HCID 22350042dichloromethane N,N-dimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.86 mL, 2.36 mmol) was added to a solution of 11-(9H-fluoren-9-ylmethoxycarbonylamino)-undecanoic acid (0.086 g, 0.194 mmol) in dichloromethane/DMF [1 mL/1 drop] and stirred at room temperature for 3 hours. The reaction mixture was evaporated, dissolved in dichloromethane [5 mL] was added dropwise to a solution of {[4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.050 g, 0.097 mmol) [example 25, step c] and triethylamine (0.03 mL, 0.19 mmol) in dichloromethane [3 mL] at room temperature and stirred for several hours. The crude reaction was evaporated and column chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (0.042 g, 47%) as a solid. ESI-MS (m/z): Calcd. for C50H58N4O7S3: 922.35; found: 923.0.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutiondissolved in dichloromethane [5 mL]
  3. stirringstirred for several hours
  4. customThe crude reaction
  5. customwas evaporated

Sources & evidence

ORD record
ord-64be1896b450486ca36051eb7f96d79f
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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