7-{3-[3-(3-Chloro-2,6-difluorophenoxy)propyl]isoxazol-5-yl}-6-[cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester → 7-{3-[3-(3-Chloro-2,6-difluorophenoxy)propyl]isoxazol-5-yl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylic acid cyclopropyl-(2,3-dichlorobenzyl)amide

HRID 1096878Notes

Reaction equation

HRID 1096878 reaction equation
C(OC([N:8]1[CH2:15][CH:14]2[N:16](C(OC(C)(C)C)=O)[CH:10]([CH2:11][C:12]([C:39]3[O:43][N:42]=[C:41]([CH2:44][CH2:45][CH2:46][O:47][C:48]4[C:53]([F:54])=[CH:52][CH:51]=[C:50]([Cl:55])[C:49]=4[F:56])[CH:40]=3)=[C:13]2[C:24](=[O:38])[N:25]([CH:35]2[CH2:37][CH2:36]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[CH2:9]1)=O)(C)(C)C.ClC(Cl)(Cl)C(NC(=O)[O-])(C)C>C1COCC1.CC(O)=O.[Zn]>[CH:35]1([N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[C:24]([C:13]2[CH:14]3[NH:16][CH:10]([CH2:11][C:12]=2[C:39]2[O:43][N:42]=[C:41]([CH2:44][CH2:45][CH2:46][O:47][C:48]4[C:53]([F:54])=[CH:52][CH:51]=[C:50]([Cl:55])[C:49]=4[F:56])[CH:40]=2)[CH2:9][NH:8][CH2:15]3)=[O:38])[CH2:37][CH2:36]1

Participants

5

Reactant 2

HCID 690881817-{3-[3-(3-Chloro-2,6-difluorophenoxy)propyl]isoxazol-5-yl}-6-[cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl esterHCID 131729530Trichloro-tert-butylcarbamate

Product 1

HCID 685708397-{3-[3-(3-Chloro-2,6-difluorophenoxy)propyl]isoxazol-5-yl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylic acid cyclopropyl-(2,3-dichlorobenzyl)amide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

This compound is prepared from compound F9, according to the above-described procedure B. After cleaving the Boc-group the trichloro-tert-butylcarbamate was cleaved using Zn-powder in THF/AcOH 3:1. LC-MS: tR=0.90 min; ES+: 637.24.

Sources & evidence

ORD record
ord-37ddbd1b0a6745f9be5e27454b229496
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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