2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazine → 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide

HRID 863325Notes

Reaction equation

HRID 863325 reaction equation
[CH2:1]([NH:5][C:6](=[O:32])[C@H:7]([CH3:31])[CH2:8][C@@H:9]1[O:13]C(C)(C)[N:11](C(OC(C)(C)C)=O)[C@H:10]1[CH2:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26]([OH:28])=O)[CH2:2][CH2:3][CH3:4].[CH3:33][O:34][CH2:35][CH2:36][CH:37]1[CH2:42][NH:41][C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[O:38]1>>[CH2:1]([NH:5][C:6](=[O:32])[C@H:7]([CH3:31])[CH2:8][C@H:9]([OH:13])[C@@H:10]([NH2:11])[CH2:23][C:24]([CH3:29])([CH3:30])[CH2:25][C:26]([N:41]1[C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[O:38][CH:37]([CH2:36][CH2:35][O:34][CH3:33])[CH2:42]1)=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 196976242(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazineHCID 867520953-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Product 1

HCID 1317205355(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide

Procedure

Starting from 230 mg of 3-[N-tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide and 193 mg of 2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazine, the title compound is obtained via (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide (analogously to Example 1a); Rf (A)=0.19; Rt (VI)=36.6/36.9 min) and 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxyethyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide (Rf (X)=0.36; Rt (VI)=30.6 min; FAB-MS: (M+H)+ =592) in a manner analogous to that described in Example 1) as a diastereomer mixture:Rf (V)=0.32; Rt (VI)=23.7/24.1 min; FAB-MS: (M+H)+ =492.

Sources & evidence

ORD record
ord-76a383791e1349f3b65a2389097bad27
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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