Ureidovaline → (2s,3s,5s)-5-(n-(n-(3-(2-Isopropyl-4-thiazolyl)propanoyl)valinyl)amino)-2-(n-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

HRID 1457140Notes

Reaction equation

HRID 1457140 reaction equation
CN(C(N[C@H](C(O)=O)C(C)C)=O)[CH2:3][C:4]1[N:5]=[C:6]([CH:9]([CH3:11])[CH3:10])[S:7][CH:8]=1.[NH2:22][C@H:23]([C:27]([NH:29][C@@H:30]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:31][C@H:32]([OH:51])[C@@H:33]([NH:41][C:42]([O:44][CH2:45][C:46]1[S:50][CH:49]=[N:48][CH:47]=1)=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:28])[CH:24]([CH3:26])[CH3:25].N[C@@H](CC1C=CC=CC=1)C[C@H](O)[C@@H](NC([O:74][CH2:75][C:76]1SC=NC=1)=O)CC1C=CC=CC=1>>[CH:9]([C:6]1[S:7][CH:8]=[C:4]([CH2:3][CH2:76][C:75]([NH:22][C@H:23]([C:27]([NH:29][C@@H:30]([CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:31][C@H:32]([OH:51])[C@@H:33]([NH:41][C:42]([O:44][CH2:45][C:46]2[S:50][CH:49]=[N:48][CH:47]=2)=[O:43])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:28])[CH:24]([CH3:26])[CH3:25])=[O:74])[N:5]=1)([CH3:10])[CH3:11]

Participants

4

Reactant 3

HCID 9818282UreidovalineHCID 111019781,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamateHCID 22863038Ritonavir EP Impurity B2×

Product 1

HCID 22862888(2s,3s,5s)-5-(n-(n-(3-(2-Isopropyl-4-thiazolyl)propanoyl)valinyl)amino)-2-(n-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

Procedure

Using the procedure of Example 1 U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with the resultant compound of Example 31 D and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with the resultant compound of Example 31 F provided, after purification by silica gel chromatography, the desired compound.

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-d0ace92d4d974f659de43fa0eeae9377
Source dataset
uspto-grants-1998_12
Patent number
US05846987

Reaction notes

Loading…