Triethylamine → N-[(benzyloxy)carbonyl]-L-phenylalanyl-N1-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl-L-alaninamide

HRID 1819894Notes

Reaction equation

HRID 1819894 reaction equation
C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH:29]([C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])[C@H:30]([C:38]([NH:40][C@H:41]([C:43]([OH:45])=O)[CH3:42])=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH:56]1[C:64]2[C:63]3[CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][C:62]=3[O:61][C:60]=2[CH:59]=[CH:58][C:57]=1[NH2:70]>>[CH2:49]([O:48][C:46]([NH:29][C@H:30]([C:38]([NH:40][C@H:41]([C:43]([NH:70][C:57]1[CH:58]=[CH:59][C:60]2[O:61][C:62]3[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65][C:63]=3[C:64]=2[CH:56]=1)=[O:45])[CH3:42])=[O:39])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:47])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 152128N-BenzyloxycarbonylphenylalanylalanineHCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 24897212N-[(benzyloxy)carbonyl]-L-phenylalanyl-N1-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl-L-alaninamideYield 25.6%

Procedure

Following the procedure of Example 30, triethylamine (0.43 mL, 3.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.31 g, 1.6 mmol), N-hydroxybenzotriazole (0.22 g, 1.6 mmol), N-Cbz-Phe-Ala-OH (0.51 g, 1.4 mmol), and 7,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine (0.25 g, 1.2 mmol) provided N-[(benzyloxy)carbonyl]-L-phenylalanyl-N1-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-yl-L-alaninamide (0.17 g). MS (ESI) m/z 554 ([M+H]+).

Sources & evidence

ORD record
ord-69030552da6e4508979411aa05ddb38b
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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