2(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide

HRID 863322Notes

Reaction equation

[CH3:1][NH:2][C:3](=[O:38])[C@@:4](N)([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:5][C@H:6]([OH:29])[C@@H:7](C(OC(C)(C)C)=O)[CH2:8][C:9]([CH3:21])([CH3:20])[CH2:10][CH2:11][O:12]CC1C=CC=CC=1.C(NC(=O)[C@H](C)C[C@H:47](O)[C@@H:48]([NH:71][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[CH2:49]C(C)(C)CC(N1C2C(=CC=CC=2)CC(COCC=C)C1)=O)CCC.C(NC(=O)[C@H](CC(C)=C)C[C@@H]1[O:94]C(C)(C=C=O)N(OC(C)(C)C)[C@H]1CC(C)(C)CCOCC1C=CC=CC=1)CCC.C(NC(=O)[C@H](C(C)C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C=CC=CC=2SC(C(NCC)=O)C1)=O)CCC>>[CH3:1][NH:2][C:3](=[O:38])[C@H:4]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:5][C@@H:6]1[O:29][C:48]([CH3:49])([CH3:47])[N:71]([C:72]([O:74][C:75]([CH3:76])([CH3:78])[CH3:77])=[O:73])[C@H:7]1[CH2:8][C:9]([CH3:20])([CH3:21])[CH2:10][C:11]([OH:12])=[O:94]

Participants

Reactant 4

HCID 867521142(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide

HCID 867521153-[N-tert-butoxy-carbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-[(2-methyl)propen-3-yl]-propionic acid (N-butyl)amide

HCID 1317205295(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

HCID 1317205345(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S)-isopropyl-7,7dimethyl-8-[2(R,S)-ethylaminocarbonyl-3,4-dihydro-2H1,4-benzothiazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 867521133-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide

Procedure

starting from 505 mg of 2(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide via 3-[N-tert-butoxycarbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide (Rf (A)=0.43; FAB-MS:(M+H)+ =567) and 3-[N-tert-butoxycarbonyl-4(S)-(2,2-dimethyl-4-hydroxybutyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzylpropionic acid (N-methyl)amide (Rf (B)=0.14; FAB-MS:(M+H)+ =477) in a manner analogous to that described in Examples 74a,74b and 74c), as the pure diastereomer: Rf (L)=0.17; FAB-MS:(M+H)+ =491.

Sources & evidence

ORD record: ord-18cb69d9c74e4aa5ad578c58607c8a13
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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