Ethyl Acetate → N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine

HRID 1493447Notes

Reaction equation

HRID 1493447 reaction equation
[CH2:1]([C@H:8]([CH2:25][C@@H:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)C(O)=O)[C:9]([NH:11][C@H](C(O)=O)COCC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][C:38]1([CH3:67])[O:42][CH:41]([CH2:43][O:44][C:45]([C@H](CC2C=CC=CC=2)C[C@@H](CC2C=CC=CC=2)C(O)=O)=[O:46])[CH2:40][O:39]1.[C:68]([O:71]CC)(=[O:70])[CH3:69]>>[CH3:37][C:38]1([CH3:67])[O:42][CH:41]([CH2:43][O:44][C:45]([C@H:26]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:25][C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([NH:11][C@H:69]([C:68]([OH:71])=[O:70])[CH2:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[O:46])[CH2:40][O:39]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 14557690N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-O-benzyl-(L)-serineHCID 149971524-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid

Product 1

HCID 86744820N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine

Procedure

To a solution of 0.5 g of (L)-homophenylalanine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester, 0.51 g of 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid is added 0.23 g of 1-(3-dimethylminopropyl)-3-ethylcarbodiimide hydrochloride. The solution is stirred overnight. The solution is diluted with ethyl acetate, washed in sequence with 1N hydrochloric acid, water, saturated sodium bicarbonate, water, dried (Na2SO4), filtered and concentrated. The residue is flash chromatographed on silica gel eluting with ethyl acetate-methylene chloride (1:4) giving N-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyryl}-(L)-homophenylalanine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester melting at 48°-50°.

Workup

  1. washwashed in sequence with 1N hydrochloric acid, water, saturated sodium bicarbonate, water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with ethyl acetate-methylene chloride (1:4)

Sources & evidence

ORD record
ord-392c1eac3545498286c37ac76e652b25
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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