Dichloromethane → 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2,5-dimethyl-1-(2-(1-methylethyl)-4-oxazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-isoxazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))-

HRID 1736601Notes

Reaction equation

HRID 1736601 reaction equation
[CH3:1][N:2]([C:12]([NH:14][C@H:15]([C:17]([OH:19])=O)[CH3:16])=[O:13])[CH2:3][C:4]1[N:5]=[C:6]([CH:9]([CH3:11])[CH3:10])[O:7][CH:8]=1.[NH2:20][C@@H:21]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:22][C@H:23]([OH:42])[C@@H:24]([NH:32][C:33]([O:35][CH2:36][C:37]1[O:41][N:40]=[CH:39][CH:38]=1)=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(Cl)Cl>CO>[CH3:1][N:2]([C:12]([NH:14][C@H:15]([C:17]([NH:20][C@@H:21]([CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:22][C@H:23]([OH:42])[C@@H:24]([NH:32][C:33]([O:35][CH2:36][C:37]1[O:41][N:40]=[CH:39][CH:38]=1)=[O:34])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:19])[CH3:16])=[O:13])[CH2:3][C:4]1[N:5]=[C:6]([CH:9]([CH3:10])[CH3:11])[O:7][CH:8]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10563897N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-alanineHCID 57164722(2S,3S,5S)-5-amino-2-(N-((5-isoxazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

Product 1

HCID 4829592,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2,5-dimethyl-1-(2-(1-methylethyl)-4-oxazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-isoxazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))-Yield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure of Example 1U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-alanine and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-5-amino-2-(N-((5-isoxazolyl)methoxy-carbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after silica gel chromatography using 92:8 CH2Cl2 : CH3OH, the desired compound (Rf 0.48, 92:8 CH2Cl2 : CH3OH)in 64% yield. 1H NMR (DMSO-d6) δ1.08 (d, 3H), 1.24 (d, 6H), 1.50 (m, 2H), 2.82 (s, 3H), 3.0(m, 1H), 4.25 (s, 2H), 4.60 (d, 1H), 5.05 (s, 2H), 6.20 (br d, 1H), 6.32 (d, 1H), 7.20 (m, 11H), 7.50 (br d, 1H), 7.78 (s, 1H), 8.51 (d, 1H). Mass spectrum: (M+H)+ =661.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-42eebab88f68479f812d9a9790199b82
Source dataset
uspto-grants-1996_07
Patent number
US05541206

Reaction notes

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