1-Hydroxybenzotriazole → HCID 68551805, compound

HRID 456348Notes

Reaction equation

HRID 456348 reaction equation
[CH:1]1([C@H:7]([NH:37][C:38]([C:40]2[CH:45]=[N:44][CH:43]=[CH:42][N:41]=2)=[O:39])[C:8]([NH:10][C@@H:11]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]([N:14]([C@H:16]2[CH2:20][N:19]([C:21](=[O:29])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][C@H:17]2[C:30]([OH:32])=O)[CH3:15])=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:65][CH:66]([CH2:75][CH2:76][CH3:77])[CH:67]([OH:74])[C:68]([NH:70][CH:71]1[CH2:73][CH2:72]1)=[O:69]>ClCCl.CCOC(C)=O>[CH:1]1([C@H:7]([NH:37][C:38]([C:40]2[CH:45]=[N:44][CH:43]=[CH:42][N:41]=2)=[O:39])[C:8]([NH:10][C@@H:11]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]([N:14]([C@H:16]2[CH2:20][N:19]([C:21]([NH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:29])[CH2:18][C@H:17]2[C:30]([NH:65][C@@H:66]([CH2:75][CH2:76][CH3:77])[CH:67]([OH:74])[C:68]([NH:70][CH:71]2[CH2:72][CH2:73]2)=[O:69])=[O:32])[CH3:15])=[O:13])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 208049823-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 68553705HCID 68553705, compound

Product 1

HCID 68551805HCID 68551805, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 48, Part A (50 mg, 0.08 mmol), N-(3-dimethyl aminopropyl)-N′-ethylcarbodiimide hydrochloride (17 mg, 0.09 mmol), 1-hydroxybenzotriazole (12 mg, 0.09 mmol), Hunig's base (42 uL, 0.24 mmol) and 3-amino-N-cyclopropyl-2-hydroxyhexanamide (WO2002018369-A2; Example 119, cpd xiii′) (15 mg, 0.08 mmol)) in dichloromethane (5 mL) was stirred for 3 hours and diluted with 100 mL EtOAc, washed with 10 mL 1 M H3PO4, 10 mL 10% NaHCO3, 20 mL with brine, dried (MgSO4), and concentrated to give the title compound (31 mg, 49%). MS (ESI+) m/z=790.7 (M+H)+.

Workup

  1. washwashed with 10 mL 1 M H3PO4, 10 mL 10% NaHCO3, 20 mL with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0466d1ff23ec4fada699622a715b7307
Source dataset
uspto-grants-2013_07
Patent number
US08497275B2

Reaction notes

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