Triethylamine → HCID 24896973, compound

HRID 1819892Notes

Reaction equation

HRID 1819892 reaction equation
C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:29]([N:36]1[CH2:43][CH2:42][CH2:41][C@H:37]1[C:38]([OH:40])=O)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[CH:44]1[C:52]2[C:51]3[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:50]=3[O:49][C:48]=2[CH:47]=[CH:46][C:45]=1[NH2:58]>>[CH:44]1[C:52]2[C:51]3[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:50]=3[O:49][C:48]=2[CH:47]=[CH:46][C:45]=1[NH:58][C:38]([C@@H:37]1[CH2:41][CH2:42][CH2:43][N:36]1[C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])=[O:40]

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 24896973HCID 24896973, compoundYield 37.6%

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-Boc-L-proline (0.29 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 (2S)-2-[(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylamino)carbonyl]pyrrolidine-1-carboxylate (0.18 g). MS (ESI) m/z 399 ([M+H]+); MS (ESI) m/z 397.3 ([M−H]−).

Sources & evidence

ORD record
ord-93fc3010d68f41dd86b81f3b407a69f5
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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