Dicyclohexylcarbodiimide → N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serine

HRID 976601Notes

Reaction equation

C[O:2][C:3](=[O:8])[C@H:4]([CH2:6][OH:7])[NH2:5].C(N(C(C)C)CC)(C)C.[N:18]1[NH:19][N:20]=[N:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:47]=[CH:46][C:32]2[N:33]([CH:36]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:37](O)=[O:38])[CH:34]=[N:35][C:31]=2[CH:30]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[O:38]=[C:37]([NH:5][C@H:4]([C:3]([OH:2])=[O:8])[CH2:6][OH:7])[CH:36]([N:33]1[C:32]2[CH:46]=[CH:47][C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22]3[N:18]=[N:19][NH:20][N:21]=3)=[CH:30][C:31]=2[N:35]=[CH:34]1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

Reactant 5

HCID 10868Dicyclohexylcarbodiimide

HCID 81531Diisopropylethylamine

HCID 2723731(S)-methyl 2-amino-3-hydroxypropanoate

HCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acid

HCID 178418300HCID 178418300, compound

Product 1

HCID 69962688N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serineYield 10.6%

Procedure

Serine methyl ester (1.0 moles, 0.119 g), diisopropylethylamine (1.0 mmoles, 0.206 g), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.0 mmoles, 0.405 g), hydroxybenzotriazole (1.0 mole, 0.135 g), and dicyclohexylcarbodiimide (1.0 moles, 0.206 g) were reacted as in Example 37. The resulting ester (0.19 moles, 0.097 g) was hydrolyzed as in Example 37 to yield 0.052 g of N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serine (MS).

Sources & evidence

ORD record: ord-616684ac8b7d490292368021d1cca804
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612360

Reaction notes

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