Sodium Carbonate → 4-(6-Hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1867953Notes

Reaction equation

HRID 1867953 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:50][C:51]1[S:52][C:53]2[CH:59]=[C:58]([OH:60])[CH:57]=[CH:56][C:54]=2[N:55]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:50][C:51]2[S:52][C:53]3[CH:59]=[C:58]([OH:60])[CH:57]=[CH:56][C:54]=3[N:55]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 334622-Amino-6-benzothiazolol2×HCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 579808374-(6-Hydroxybenzothiazol-2-ylcarbamoyl)piperidine-1-carboxylic acid tert-butyl esterYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (276 mg, 1.203 mmol), of HATU (549 mg, 1.444 mmol) and of diisopropylethylamine (187 mg, 1.44 mmol) in 3 ml of DMF is stirred at room temperature for 15 minutes. The 2-aminobenzothiazol-6-ol (intermediate 1) (200 mg, 1.203 mmol) dissolved in 3 ml of DMF is added in a single portion. The reaction medium is stirred at room temperature for 2 hours, poured into a 10% solution of Na2CO3 in water (20 ml) and extracted with ethyl acetate. The crude reaction product is purified by column chromatography (eluent: EtOAc/heptane (1/1)) to give 401 mg of 4-(6-hydroxybenzothiazol-2-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (white solid).

Workup

  1. additionis added in a single portion
  2. extractionextracted with ethyl acetate
  3. customThe crude reaction product
  4. customis purified by column chromatography (eluent: EtOAc/heptane (1/1))

Sources & evidence

ORD record
ord-616a751f903b45ab9fc3fbcbab4f00eb
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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