Dicyclohexylcarbodiimide → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoate

HRID 720932

Reaction equation

HRID 720932 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:45][C:46]([NH:48][CH:49]1[C:59]2[CH:60]=[C:61](O)[CH:62]=[CH:63][C:58]=2[C:57]2[C:52](=[CH:53][C:54]([O:69][CH3:70])=[C:55]([O:67][CH3:68])[C:56]=2[O:65][CH3:66])[CH2:51][CH2:50]1)=[O:47]>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C:61]1[CH:62]=[CH:63][C:58]2[C:57]3[C:56]([O:65][CH3:66])=[C:55]([O:67][CH3:68])[C:54]([O:69][CH3:70])=[CH:53][C:52]=3[CH2:51][CH2:50][C@H:49]([NH:48][C:46](=[O:47])[CH3:45])[C:59]=2[CH:60]=1)=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 97865N-AcetylcolchicinolHCID 544618583-{[(2r)-2,6-Di(tertbutoxycarbonylamino)hexanoyl]amino}propanoic acid

Product 1

HCID 69586384(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoateYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoic acid (2) (0.178 g; 0.5 mmol), DCCI (0.124 g; 0.6 mmol), DMAP (0.013 g; 0.1 mmol) and N-acetyl-colchicinol (0.25 g; 1.2 mmol) in dichloromethane was stirred under argon atmosphere at ambient temperature for 5 hours. After filtration of the insoluble material the residue was purified by flash chromatography eluting with dichloromethane/ethanol (95/5) to give (1).

Workup

  1. filtrationAfter filtration of the insoluble material the residue
  2. customwas purified by flash chromatography
  3. washeluting with dichloromethane/ethanol (95/5)

Sources & evidence

ORD record
ord-114634f21c3a4a9fa0eecc265ffb4bb8
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Linked notes

Loading…