Benzyl Alcohol → HCID 178520449, compound

HRID 1783441Notes

Reaction equation

HRID 1783441 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](/[N:11]=[C:12](/[NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]2[C:20](=[O:21])[NH:19][C@@H:18]2[C:22]([OH:24])=[O:23])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:36](O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][C:9](/[N:11]=[C:12](/[NH:25][C:26](=[O:35])[CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]2[C:20](=[O:21])[NH:19][C@@H:18]2[C:22]([O:24][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:23])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178520450HCID 178520450, compound

Product 1

HCID 178520449HCID 178520449, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 148 (74 mg, 1.0 eq.) in DMF (1.5 mL) was added benzyl alcohol (19 uL, 1.2 eq.), EDC-HCl (35 mg, 1.2 eq.), HOBt (24 mg, 1.2 eq.) and DIEA (60 μL eq.). The reaction was stirred at room temperature for 16 hours and then diluted with ethyl acetate and washed with 1N HCl. The aqueous layer was then washed with ethyl acetate (2×10 mL). The combined organics were then washed with saturated NaHCO3 (2×10 mL), water (10 mL), dried over magnesium sulfate and concentrated in vacuo to give the crude product (55 mg) as a colorless oil. The product was purified by silica gel chromatography using a gradient elution from 20% EtOAc in hexanes to 50% EtOAc in hexanes to yield 149 (50 mg).

Workup

  1. washwashed with 1N HCl
  2. washThe aqueous layer was then washed with ethyl acetate (2×10 mL)
  3. washThe combined organics were then washed with saturated NaHCO3 (2×10 mL), water (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give the crude product (55 mg) as a colorless oil
  7. customThe product was purified by silica gel chromatography
  8. washa gradient elution from 20% EtOAc in hexanes to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-da54d3c9ece84e808cacb59e3ff66d48
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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