Hydrochloric Acid → 1-[(2S,3S)-3-{N2-[4-(Benzyloxycarbonylamino)phenoxyacetyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide

HRID 1780246Notes

Reaction equation

HRID 1780246 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:24][C@H:25]([C:30]([NH:32][C@@H:33]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C@H:34]([OH:49])[C:35]([N:37]1[CH2:48][CH2:47][CH2:46][C@H:38]1[C:39]([NH:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:36])=[O:31])[CH2:26][C:27](=[O:29])[NH2:28].C(OC(N[C@H](C(N[C@@H](CC1C=CC=CC=1)[C@H](O)C(N1CCC[C@H]1C(NC(C)(C)C)=O)=O)=O)CC(=O)N)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]([NH:24][C@H:25]([C:30]([NH:32][C@@H:33]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@H:34]([OH:49])[C:35]([N:37]2[CH2:48][CH2:47][CH2:46][C@H:38]2[C:39]([NH:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:36])=[O:31])[CH2:26][C:27](=[O:29])[NH2:28])=[O:20])=[CH:21][CH:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 105549081-[(2S,3S)-3-(N2-t-Butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamideHCID 190498322-(4-(((Benzyloxy)carbonyl)amino)phenoxy)acetic acidHCID 677227821-[(2S,3S)-3-L-asparaginylamino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride

Product 1

HCID 700489921-[(2S,3S)-3-{N2-[4-(Benzyloxycarbonylamino)phenoxyacetyl]-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following a procedure similar to that described in Example 14, but using 99.8 mg (0.33 mmol) of 4-(benzyloxycarbonylamino)phenoxyacetic acid (prepared as described in Preparation 15) and 150 mg (0.30 mmol) of 1-[(2S,3S)-3-(L-asparaginylamino)-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide hydrochloride {prepared by treating 1-[(2S,3S)-3-(N2 -t-butoxycarbonyl-L-asparaginyl)amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide, the compound prepared as described in Example 15, with a 4N solution of hydrogen chloride in dioxane), 164 mg of the title compound were obtained as a white powder, melting at 103°-105° C.

Workup

  1. customprepared
  2. customthe compound prepared

Sources & evidence

ORD record
ord-e89a5a81c2ac465d8ff00683afb580ac
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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