Triethylamine → HCID 24896969, compound

HRID 1819887Notes

Reaction equation

C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:29]([NH:39][C@H:40]([C:42]([OH:44])=O)[CH3:41])([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].[CH:45]1[C:53]2[C:52]3[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:51]=3[O:50][C:49]=2[CH:48]=[CH:47][C:46]=1[NH2:59]>>[CH3:41][C@H:40]([NH:39][C:29](=[O:30])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:42](=[O:44])[NH:59][C:46]1[CH:47]=[CH:48][C:49]2[O:50][C:51]3[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][C:52]=3[C:53]=2[CH:45]=1

Participants

Reactant 5

HCID 8471Triethylamine

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

HCID 757711-Hydroxybenzotriazole

HCID 736104N-carbobenzyloxyalanine

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

Product 1

HCID 24896969HCID 24896969, compoundYield 13.1%

Procedure

Following the procedure of Example 30, triethylamine (0.52 mL, 3.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.37 g, 1.9 mmol), N-hydroxybenzotriazole (0.26 g, 1.9 mmol), N-carbobenzyloxy-L-alanine (0.37 g, 1.6 mmol), and 7,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine (0.30 g, 1.5 mmol) provided benzyl [(1S)-1-methyl-2-oxo-2-(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylamino)ethyl]carbamate (0.08 g) after purification by flash column chromatography (elution with 40% ethyl acetate-hexanes). MS (ES) m/z 407.2 ([M+H]+).

Sources & evidence

ORD record: ord-a884833e52c143f39f29692de4c46a46
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601856B2

Reaction notes

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