1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate → 2-Chloro-4-[(3aR,4R)-4-hydroxy-1,1-dioxohexahydrothia-2,6a-diazapentalen-2-yl]-3-methylbenzonitrile

HRID 1669914Notes

Reaction equation

HRID 1669914 reaction equation
COC([C@@H]1[C@H](O)CCN1C(OC(C)(C)C)=O)=O.C(OC(N1CC[C@H](O[Si](C(C)(C)C)(C)C)[C@H]1CO)=O)(C)(C)C.[OH:40][C@H:41]1[CH2:48][CH2:47][N:46]2[C@@H:42]1[CH2:43][N:44]([C:51]1[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[C:53]([Cl:59])[C:52]=1[CH3:60])[S:45]2(=[O:50])=[O:49]>>[Cl:59][C:53]1[C:52]([CH3:60])=[C:51]([N:44]2[CH2:43][C@H:42]3[N:46]([CH2:47][CH2:48][C@H:41]3[OH:40])[S:45]2(=[O:49])=[O:50])[CH:58]=[CH:57][C:54]=1[C:55]#[N:56]

Participants

4

Reactant 3

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylateHCID 109885451,2-Pyrrolidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,3S)-rel-HCID 116599004-[(3aR,4S)-4-Hydroxy-1,1-dioxohexahydrothia-2,6a-diazapentalen-2-yl]-2-chloro-3-methylbenzonitrile

Product 1

HCID 116955742-Chloro-4-[(3aR,4R)-4-hydroxy-1,1-dioxohexahydrothia-2,6a-diazapentalen-2-yl]-3-methylbenzonitrile

Procedure

The title compound was prepared from (2S,3R)—N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester by procedures analogous to those described in Example 7 (7A to 7F). HRMS (ES) m/z 328.0528 [M+1]+.

Sources & evidence

ORD record
ord-174393d7b70a4bd8a0d907b3916b6c29
Source dataset
uspto-grants-2011_08
Patent number
US07989640B2

Reaction notes

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