Benzyloxycarbonylglycine → HCID 15837643, compound

HRID 1599382Notes

Reaction equation

HRID 1599382 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])=[CH:3][CH:2]=1.[CH3:16][O:17][C:18](=[O:31])[C@@H:19]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)[NH:20]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:16][O:17][C:18](=[O:31])[C@@H:19]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)[N:20]1[C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:10]

Participants

6

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 15837642HCID 15837642, compound

Product 1

HCID 15837643HCID 15837643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of Z-glycine dissolved in dichloromethane is coupled with 0.83 g of 5-(meta-hydroxyphenyl)proline methyl ester in the presence of 2.06 g of PyBrOP and 2.6 ml of diisopropylethylamine. After stirring for 4 hours at room temperature, the organic phase is washed (sodium hydrogen carbonate, water, citric acid, water), dried over sodium sulphate, filtered and evaporated to dryness. The oily residue is chromatographed on silica gel (n-hexane/ethyl acetate. 4:6). A white solid corresponding to the expected product is obtained.

Workup

  1. washthe organic phase is washed (sodium hydrogen carbonate, water, citric acid, water)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe oily residue is chromatographed on silica gel (n-hexane/ethyl acetate. 4:6)

Sources & evidence

ORD record
ord-22a620261bf8411f820ac0b56ea7c0ae
Source dataset
uspto-grants-1998_04
Patent number
US05741781

Reaction notes

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