Diethyl Ether → HCID 42641556, compound

HRID 600335Notes

Reaction equation

HRID 600335 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C@H:27]([NH:30][C:31]([C@@H:33]4[CH2:38][CH2:37][CH2:36][CH2:35][N:34]4C(OC(C)(C)C)=O)=[O:32])[C:28]#[N:29])=[CH:22][CH:21]=3)=[CH:19][C:14]=2[S:13][C:12]1=[O:46])(C(C)(C)C)(C)C.C(OCC)C>C(O)=O>[C:28]([C@@H:27]([NH:30][C:31]([C@@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][NH:34]1)=[O:32])[CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[CH:17]=[CH:16][C:15]3[N:11]([CH2:10][CH2:9][OH:8])[C:12](=[O:46])[S:13][C:14]=3[CH:19]=2)=[CH:25][CH:24]=1)#[N:29]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 57999640HCID 57999640, compound

Product 1

HCID 42641556HCID 42641556, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (S)-tert-butyl 2-((S)-2-(4-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)phenyl)-1-cyanoethylcarbamoyl)piperidine-1-carboxylate (103 mg) in formic acid (1 ml) was stirred at 50° C. for 10 min. The solvent was removed in vacuo and the residue was purified by flash silica chromatography eluting with 1:14 2M ammonia in methanol/DCM to give, after trituration with diethyl ether, the title compound (60 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash silica chromatography
  3. washeluting with 1:14 2M ammonia in methanol/DCM
  4. customto give

Sources & evidence

ORD record
ord-461ab367473544e5ace40345d2e1d0e9
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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