Trifluoroacetic acid → HCID 15481644, compound

HRID 1954681Notes

Reaction equation

HRID 1954681 reaction equation
[N:1]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:2]1[C:3]([N:5]([CH2:14][CH3:15])[CH2:6][C:7]([O:9]C(C)(C)C)=[O:8])=[O:4].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[N:1]1([C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:2]1[C:3]([N:5]([CH2:14][CH3:15])[CH2:6][C:7]([OH:9])=[O:8])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 15481643HCID 15481643, compound

Product 1

HCID 15481644HCID 15481644, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Cbz-D-hPro-N(Et)Gly-O-t-Bu (5 g, 12.4 mmol) in dichloromethane (50 mL) was added anisole (2.5 mL) and trifluoroacetic acid (50 mL). The mixture was allowed to stir for several hours at room temperature. The solvents were removed in vacuo and the resulting oil was partitioned between saturated aqueous NaHCO3 and diethyl ether. The layers were separated and the organic phase was extracted once with saturated aqueous NaHCO3. The combined aqueous phase was adjusted to pH 2 with 5N aqueous HCl and extracted three times with ethyl acetate (150 mL). The combined ethyl acetate extracts were dried with MgSO4, filtered, and concentrated to give a colorless oil (4.6 g, 106%).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe resulting oil was partitioned between saturated aqueous NaHCO3 and diethyl ether
  3. customThe layers were separated
  4. extractionthe organic phase was extracted once with saturated aqueous NaHCO3
  5. extractionextracted three times with ethyl acetate (150 mL)
  6. dry with materialThe combined ethyl acetate extracts were dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bda123b3c8674b18a5ecd726ce50a8ee
Source dataset
uspto-grants-2000_09
Patent number
US06124277

Reaction notes

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