Acetonitrile → (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester

HRID 1082151Notes

Reaction equation

HRID 1082151 reaction equation
[C:1]([O:20][C@@H:21](C)C(O)=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][O:28][C:29](=[O:34])[C@H:30]([CH2:32][SH:33])[NH2:31].CN1CC[O:39][CH2:38]C1.[C:42](#N)[CH3:43]>>[CH3:27][O:28][C:29](=[O:34])[C@@H:30]([NH:31][C:38](=[O:39])[C@@H:42]([CH3:43])[CH2:21][O:20][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:32][SH:33]

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 79724-MethylmorpholineHCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 54161083(S)-2-trityloxypropionic acid

Product 1

HCID 54008528(R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester

Procedure

To a suspension of 9.97 g of (S)-2-trityloxy-propionic acid, 5.60 g of L-cysteine methyl ester hydrochloride and 6.6 g of N-(3-dimethyl-aminopropyl)-N'-ethylcarbodiimide hydrochloride in 50 ml acetonitrile was added over 10 min a solution of 6.9 g of 4-methyl-morpholine in 50 ml of acetonitrile. The mixture was stirred at room temperature for 3 h and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent to yield 2.30 g of (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester as amorphous solid.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-159dbb406b4c42a1ae5df24048c2f588
Source dataset
uspto-grants-1996_12
Patent number
US05589473

Reaction notes

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