Triethylamine → HCID 24896738, compound

HRID 1819889Notes

Reaction equation

C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:29]([NH:36][CH2:37][C:38]([OH:40])=O)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[CH:41]1[C:49]2[C:48]3[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:47]=3[O:46][C:45]=2[CH:44]=[CH:43][C:42]=1[NH2:55]>>[O:40]=[C:38]([NH:55][C:42]1[CH:43]=[CH:44][C:45]2[O:46][C:47]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][C:48]=3[C:49]=2[CH:41]=1)[CH2:37][NH:36][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35]

Participants

Reactant 5

HCID 8471Triethylamine

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 78288N-(tert-butoxycarbonyl)glycine

HCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 24896738HCID 24896738, compoundYield 46.5%

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-glycine (0.24 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 [2-oxo-2-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylamino)ethyl]carbamate (0.20 g). MS (ESI) m/z 359 ([M+H]+); MS (ESI) m/z 357.2 ([M−H]−).

Sources & evidence

ORD record: ord-1a8f18ab6f954313ae9c3180d06f4bcb
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601856B2

Reaction notes

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