1,2-Dichloroethane → HCID 70171832, compound

HRID 2306178Notes

Reaction equation

HRID 2306178 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[C:11]([O:15][C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:11]([O:15][C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][N:21]([C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[CH:3]=2)[CH2:20]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 74203-Hydroxybenzoic AcidHCID 81531DiisopropylethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 70171832HCID 70171832, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzoic acid (500 mg, 3.62 mmol), (R)-3-(tert-butoxycarbonylamino)pyrrolidine (708 mg, 3.80 mmol), EDC (729 mg, 3.80 mmol), 1-hydroxybenzotriazole hydrate (514 mg, 3.80 mmol), and N,N-diisopropylethylamine (631 mL, 3.62 mmol) were combined in DMF (20 mL) and the mixture was stirred at ambient temperature for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted further with CH2Cl2 (2×25 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with CH2Cl2—3% MeOH—0.3% NH4OH to yield the titled product as a white foam.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 (25 mL) and CH2Cl2 (50 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (2×25 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica
  8. washeluting with CH2Cl2—3% MeOH—0.3% NH4OH

Sources & evidence

ORD record
ord-6e2f8c0864164b01b63a7233b9222761
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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