N-(tert-butoxycarbonyl)glycine → HCID 71668135, compound

HRID 624673Notes

Reaction equation

HRID 624673 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[S:31][C:12]3=[N:13][C:14]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)=[CH:15][C:16](=[O:17])[N:11]3[N:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[NH:32](C(OC(C)(C)C)=O)[CH2:33][C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:32][CH2:33][C:34]([NH:1][C:2]1[CH:3]=[C:4]([C:9]2[S:31][C:12]3=[N:13][C:14]([N:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)=[CH:15][C:16](=[O:17])[N:11]3[N:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1)=[O:35]

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89705355HCID 89705355, compound

Product 1

HCID 71668135HCID 71668135, compoundYield 120.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-(3-amino-5-bromophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (30.0 mg, 0.059 mmol) in DMF (2 ml) are added Boc-Gly-OH (20.7 mg, 0.118 mmol), HATU (45.0 mg, 0.118 mmol) and i−Pr2NEt (31 μl, 0.177 mmol). The mixture is stirred at room temperature for 2 h. EtOAc (10 ml) is added and the solution is washed with H2O and brine. The organic layer is dried over Na2SO4. After removing EtOAc, the residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/20 gradient) to give the desired product (33 mg, 84%).

Workup

  1. washthe solution is washed with H2O and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customAfter removing EtOAc
  4. customthe residue is purified by Biotage column chromatography (MeOH/DCM: 1/100 to 1/20 gradient)

Sources & evidence

ORD record
ord-4788668ce76445bfa89a7672eebbbcbf
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

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