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

HRID 720931Notes

Reaction equation

HRID 720931 reaction equation
C(OC([NH:8][C@H:9]([CH2:43][CH2:44][CH2:45][CH2:46][NH:47]C(OC(C)(C)C)=O)[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27]3[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=3[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1)=[O:16])=[O:11])=O)(C)(C)C.Cl.CCOCC>ClCCl>[NH2:8][C@H:9]([CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27]3[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=3[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1)=[O:16])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 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}propanoate

Product 1

HCID 58658612(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-diaminohexanoyl]amino}propanoateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (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 (1) (0.123 g; 0.162 mmol) in dichloromethane (10 ml) was treated with a 4.8M solution of hydrogen chloride in ether (170 μl; 0.81 mmol). The mixture was stirred at ambient temperature for 1 hour and the resulting precipitate was filtered, washed with ether and dried to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-diaminohexanoyl]amino}propanoate as a white solid.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-1286b4c261d14de9aeaff7ec55980896
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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