Triethylamine → HCID 24896971, compound

HRID 1819891Notes

Reaction equation

HRID 1819891 reaction equation
C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:29]([NH:36][C@H:37]([C:45]([OH:47])=O)[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[CH:48]1[C:56]2[C:55]3[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][C:54]=3[O:53][C:52]=2[CH:51]=[CH:50][C:49]=1[NH2:62]>>[CH2:38]([C@H:37]([NH:36][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[C:45](=[O:47])[NH:62][C:49]1[CH:50]=[CH:51][C:52]2[O:53][C:54]3[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][C:55]=3[C:56]=2[CH:48]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 24896971HCID 24896971, compoundYield 39%

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-Boc-L-phenylalanine (0.36 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 tert-butyl [(1S)-1-benzyl-2-oxo-2-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylamino)ethyl]carbamate (0.21 g). MS (ESI) m/z 449 ([M+H]+); MS (ESI) m/z 447.3 ([M−H]−).

Sources & evidence

ORD record
ord-3c2f884e8ac748aebdfe4c08da531a64
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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