1-Hydroxybenzotriazole hydrate → HCID 10229408, compound

HRID 2223100Notes

Reaction equation

HRID 2223100 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1.C1(N=C=N)CCCCC1.O.ON1C2C=CC=CC=2N=N1.[NH2:35][CH2:36][C:37]([C:40]1[O:44][C:43]([C:45]2[CH:46]=[CH:47][C:48]([Cl:52])=[C:49]([OH:51])[CH:50]=2)=[C:42]([C:53]2[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=2)[CH:41]=1)([CH3:39])[CH3:38]>CN(C=O)C>[Cl:52][C:48]1[CH:47]=[CH:46][C:45]([C:43]2[O:44][C:40]([C:37]([CH3:39])([CH3:38])[CH2:36][NH:35][C:12]([CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][O:3][CH3:2])[CH2:11][CH2:10]3)=[O:14])=[CH:41][C:42]=2[C:53]2[CH:54]=[CH:55][N:56]=[CH:57][CH:58]=2)=[CH:50][C:49]=1[OH:51]

Participants

6

Reactant 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 9967912HCID 9967912, compoundHCID 12048208N-CyclohexylcarbodiimideHCID 450750321-(2-Methoxyethyl)piperidine-4-carboxylic acid hydrochloride

Product 1

HCID 10229408HCID 10229408, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of the product of Example 4 Step 2 (265 mg, 1.18 mmol) in DMF (5 ml) was treated with N-cyclohexylcarbodiimide, N′-methyl polystyrene (1.8 g) and 1-hydroxybenzotriazole hydrate (162 mg, 1.19 mmol). The mixture was stirred at room temperature for 30 minutes and then treated with a solution of the product of Example 3 Step 2 (407 mg, 1.19 mmol) in DMF (2 ml). After stirring for a further 16 hours, the reaction mixture was applied to a Bond Elut SCX cartridge. The cartridge was eluted with methanol and then 0.880 ammonia solution/methanol (1:9) to elute the product. After concentrating in vacuo, the product was purified further by chromatography on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1) to yield the title compound (340 mg, 56%); MS (ES+) m/e 512, 514 [M+H]+.

Workup

  1. stirringAfter stirring for a further 16 hours
  2. washThe cartridge was eluted with methanol
  3. wash0.880 ammonia solution/methanol (1:9) to elute the product
  4. concentrationAfter concentrating in vacuo
  5. customthe product was purified further by chromatography on silica gel eluting with chloroform/ethanol/0.880 ammonia solution (90:9:1)

Sources & evidence

ORD record
ord-d84399dab3c44a7683547c6875856641
Source dataset
uspto-grants-2008_05
Patent number
US07375105B2

Reaction notes

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