Triethylamine → Tert-butyl {(1r,2r)-2-(benzyloxy)-1-[(7,8,9,10-tetrahydro-6h-benzo[b]cyclohepta[d]furan-2-ylamino)carbonyl]propyl}carbamate

HRID 1819895Notes

Reaction equation

HRID 1819895 reaction equation
C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH:29]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@@H:30]([C:41]([OH:43])=O)[C@H:31]([CH3:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH:51]1[C:59]2[C:58]3[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][C:57]=3[O:56][C:55]=2[CH:54]=[CH:53][C:52]=1[NH2:65]>>[CH2:33]([O:32][C@H:31]([CH3:40])[C@@H:30]([NH:29][C:44](=[O:45])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:41]([NH:65][C:52]1[CH:53]=[CH:54][C:55]2[O:56][C:57]3[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][C:58]=3[C:59]=2[CH:51]=1)=[O:43])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6992573(2R,3S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}butanoic acidHCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 24897211Tert-butyl {(1r,2r)-2-(benzyloxy)-1-[(7,8,9,10-tetrahydro-6h-benzo[b]cyclohepta[d]furan-2-ylamino)carbonyl]propyl}carbamateYield 18.6%

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-D-Thr(Bzl)-OH (0.42 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 {(1R,2R)-2-(benzyloxy)-1-[(7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylamino)carbonyl]propyl}carbamate (0.11 g). MS (ESI) m/z 493 ([M+H]+); MS (ESI) m/z 491 ([M−H]−).

Sources & evidence

ORD record
ord-1ce9c49de14842d7a9cf28823ed45fb6
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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