Triethylamine → 6-[5-(2-Oxo-Hexahydro-Thieno[3,4-D]Imidazol-4-Yl)-Pentanoylamino]-Hexanoic Acid

HRID 1464800

Reaction equation

HRID 1464800 reaction equation
Cl.COC(=O)CCCCCN.[C:12]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])(=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C@@H:25]2[C@@H:20]([NH:21][C:22]([NH:24]2)=[O:23])[CH2:19][S:18]1.NC1C=C2C(C([Cl:57])=C(OCCC3C=CC=CC=3)OC2=O)=CC=1.CCN(CC)CC>S(Cl)(Cl)=O.O>[C:12]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])(=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C@@H:25]2[C@@H:20]([NH:21][C:22]([NH:24]2)=[O:23])[CH2:19][S:18]1.[C:12]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([Cl:57])=[O:35])(=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C@@H:25]2[C@@H:20]([NH:21][C:22]([NH:24]2)=[O:23])[CH2:19][S:18]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 4469056-[5-(2-Oxo-Hexahydro-Thieno[3,4-D]Imidazol-4-Yl)-Pentanoylamino]-Hexanoic AcidHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 13654068HCID 13654068, compound

Product 2

HCID 4469056-[5-(2-Oxo-Hexahydro-Thieno[3,4-D]Imidazol-4-Yl)-Pentanoylamino]-Hexanoic AcidHCID 54466620HCID 54466620, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

6-(Biotinylamino)caproic acid was prepared from N-hydroxysuccinimido biotinate (Jasiewicz et al., Exp. Cell Res. 100, pp 213-217 (1976)) and 6-aminocaproic acid methyl ester hydrochloride by a previously described method (Hofmann et al., Biochemistry 23, pp 2547-2553 (1984)). 6-(Biotinylamino)caproic acid chloride was prepared by incubating 6-(biotinylamino)caproic acid (0.36 g, 1 mmole) in 4 ml of thionyl chloride at 25°-35° C. for 1 h, and excess thionyl chloride was removed under reduced pressure. The residue was dissolved in DMF and 7-amino-4-chloro-3-(2-phenylethoxy)isocoumarin (0.34 g, 1 mmole) and Et3N (0.1 g, 1 mmole) were added and the reaction mixture was stirred at r.t. overnight. The product was purified from column chromatography and eluted with CH2Cl2 :MeOH=10:1, yield, 28%, mp 163°-167° C., NMR was consistent with the assigned structure, mass spectra (FAB+) m/e=655 (M+1). Anal. Calc. for C33H39N4O6ClS.H2O: C, 58.87; H, 6.14; N, 8.32; Cl, 5.27. Found: C, 58.72; H, 6.22; N, 8.90; Cl, 5.50.

Workup

  1. customat 25°-35° C.
  2. customfor 1 h
  3. customexcess thionyl chloride was removed under reduced pressure
  4. dissolutionThe residue was dissolved in DMF
  5. customThe product was purified from column chromatography
  6. washeluted with CH2Cl2
  7. customMeOH=10:1, yield

Sources & evidence

ORD record
ord-60709878962445688bdd6e068784e906
Source dataset
uspto-grants-1994_04
Patent number
US05306824

Linked notes

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