Triethylamine → HCID 22990562, compound

HRID 1169292Notes

Reaction equation

HRID 1169292 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:27]=[CH:26][C:25]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30][CH:29]=2)=[CH:24][C:18]=1[O:19][CH2:20][C:21](O)=[O:22])[C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:47]=[CH:48][CH:49]=1)[C:42]([O:44][CH2:45]C)=[O:43].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC>CN(C=O)C>[CH2:1]([N:8]([CH2:16][C:17]1[CH:27]=[CH:26][C:25]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30][CH:29]=2)=[CH:24][C:18]=1[O:19][CH2:20][C:21]([NH:38][C:39]1[CH:40]=[C:41]([CH:47]=[CH:48][CH:49]=1)[C:42]([O:44][CH3:45])=[O:43])=[O:22])[C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22990557HCID 22990557, compound

Product 1

HCID 22990562HCID 22990562, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A room temperature solution of Example 21A (50 mg, 0.10 mmol) in DMF (1.0 mL) was treated with ethyl 3-aminobenzoate (20 μL, 0.13 mmol), HOBT (23 mg, 0.14 mmol), EDCI (29 mg, 0.15 mmol), and Et3N (21 μL, 0.15 mmol), stirred for 5 hours, and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:5 hexanes/ethyl acetate to provide the desired product.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 2:5 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-01ce53c80af34bc18420c4d9d8f3313c
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

Loading…