Sodium Bicarbonate → benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

HRID 2395100Notes

Reaction equation

HRID 2395100 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26].[CH2:41]([O:48][C:49]([NH:51][C@H:52]([C:54](O)=[O:55])[CH3:53])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:41]([O:48][C:49]([NH:51][C@H:52]([C:54]([NH:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26])=[O:55])[CH3:53])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 736104N-carbobenzyloxyalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18972493Benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate

Product 1

HCID 67645508benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetateYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.35 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate in 70 ml of acetonitrile was cooled to 0° and treated with 0.15 g of N-benzyloxycarbonyl-L-alanine. A total of 0.36 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate and 0.17 g of sodium bicarbonate were added in several portions. The reaction mixture was stirred for a total of 36 hours and thereby warmed to room temperature, whereupon it was diluted with ice-water and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulphate and concentrated. The residue was chromatographed several times over silica gel in chloroform/methanol, whereby 0.33 g of benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained as a colourless foam; IR 1728, 1673, 1605, 1494 cm-1.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed several times over silica gel in chloroform/methanol

Sources & evidence

ORD record
ord-cf47939c95554e138e0e31fc8c72b263
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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