Sodium Hydroxide → 3-{2-[(Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-1,3-thiazol-4-yl}propanoic acid

HRID 877262Notes

Reaction equation

HRID 877262 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])[N:6]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH:45]1([CH:50]([C:54]2[CH:59]=[CH:58][C:57]([CH2:60][N:61]3[C:66](=[O:67])[CH2:65][O:64][C:63]([C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)=[N:62]3)=[CH:56][CH:55]=2)[C:51](O)=[O:52])[CH2:49][CH2:48][CH2:47][CH2:46]1.[OH-].[Na+]>CS(C)=O>[CH:45]1([CH:50]([C:54]2[CH:59]=[CH:58][C:57]([CH2:60][N:61]3[C:66](=[O:67])[CH2:65][O:64][C:63]([C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)=[N:62]3)=[CH:56][CH:55]=2)[C:51]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[N:6]=2)=[O:52])[CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11310165Ethyl 3-(2-amino-1,3-thiazol-4-yl)propanoateHCID 58074507cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid

Product 1

HCID 581366473-{2-[(Cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-1,3-thiazol-4-yl}propanoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

20 mg (0.1 mmol) of ethyl 3-(2-amino-1,3-thiazol-4-yl)propanoate [Beilstein Reg. No. 9762098], 41.7 mg (0.13 mmol) of TBTU and 25.8 mg of ethyldiisopropylamine were added to a solution of 39.2 mg (0.1 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetic acid (Example 51A) in 0.5 ml DMSO. The mixture was stirred at room temperature overnight. 0.3 ml of 2 M aqueous sodium hydroxide solution was then added, and the mixture was once more stirred overnight. The solvent was then evaporated, and the residue obtained was purified directly by preparative HPLC/MS. This gave 7.1 mg (0.013 mmol, 13% of theory) of the title compound.

Workup

  1. stirringthe mixture was once more stirred overnight
  2. customThe solvent was then evaporated
  3. customthe residue obtained
  4. customwas purified directly by preparative HPLC/MS

Sources & evidence

ORD record
ord-2f09242a04fc43dbb3e7b7314aa1bdce
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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