Succinic anhydride → HCID 131721605, compound

HRID 850204Notes

Reaction equation

HRID 850204 reaction equation
C(OC(=O)[C@H](CO)N[C:9](=[O:29])[CH2:10][N:11]([NH:13][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]1[C@@H:27]2[C@@H:22]([NH:23][C:24]([NH:26]2)=[O:25])[CH2:21][S:20]1)[CH3:12])(C)(C)C.C(N(CC)CC)C.C1(=O)O[C:43](=[O:44])CC1>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:43][O:44][C:9](=[O:29])[CH2:10][N:11]([NH:13][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]1[C@@H:27]2[C@@H:22]([NH:23][C:24]([NH:26]2)=[O:25])[CH2:21][S:20]1)[CH3:12]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131721606HCID 131721606, compound

Product 1

HCID 131721605HCID 131721605, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
12.5 °C

Procedure

To a solution of biotinamido-N-methylglycyl-serine t-butyl ester (6) in anhydrous dimethylformamide is added 3 equivalents of triethylamine, 0.01-0.1 equivalents of 4-dimethylaminopyridine and 1.1 equivalents of succinic anhydride. The mixture is stirred at 0-25° C. for 20-24 h and then concentrated via reduced pressure rotary evaporation. The residue is diluted with ethyl acetate and 1 N aqueous hydrochloric acid. The organic phase is then dried over magnesium sulfate, filtered and concentrated. The residue is chromatographed on reverse phase C-18 silica gel, eluting with methanol/water. The fractions containing the product are combined and concentrated to give the final product (4).

Workup

  1. concentrationconcentrated via reduced pressure rotary evaporation
  2. additionThe residue is diluted with ethyl acetate and 1 N aqueous hydrochloric acid
  3. dry with materialThe organic phase is then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed on reverse phase C-18 silica gel
  7. washeluting with methanol/water
  8. additionThe fractions containing the product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ecb06549a8154b14a70008518095c13f
Source dataset
uspto-grants-2000_01
Patent number
US06015897

Reaction notes

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