Trifluoroacetic acid → HCID 70183046, compound

HRID 1462317Notes

Reaction equation

HRID 1462317 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][NH:11][C:12](=[O:22])[CH2:13][NH:14]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>CCOCC>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[CH2:1]([O:8][C:9](=[O:23])[CH2:10][NH:11][C:12](=[O:22])[CH2:13][NH2:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3244524Benzyl (tert-butoxycarbonyl)glycylglycinate

Product 1

HCID 70183046HCID 70183046, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Nα -t-butyloxycarbonyl-glycyl-glycine benzyl ester (3.22 g, 10 mmol) was dissolved in TFAOH -trifluoracetic acid - (30 ml) at 20° C. and left to stand for 2 h. After evaporation to dryness at 20° C. under reduced pressure, the glycyl-glycine benzyl ester trifluoracetate (3.23 g, 9.6 mmol) was obtained as a solid by trituration of the residual oil in ether and was coupled to Nα -BOC-aspartic acid β-t-butyl ester (2.78 g, 9.6 mmol) according to the procedure described for the preparation of dipeptide of formula V. After the usual work-up, the product which could not be induced to crystallize, was obtained after evaporation of the solvent (ethyl acetate) and drying as a foam. Analysis: calculated for C24H35N3O8 : C, 58.40; H, 7.15; N,8.52. Pound: C, 58.20; H, 7.19; N, 8.48. [Rf : 0.52 from chloroform: methanol (20:1)]. The yield was 4.50 g (95 %).

Workup

  1. waitleft
  2. customAfter evaporation to dryness at 20° C. under reduced pressure

Sources & evidence

ORD record
ord-97eaaa260e3f4758b6682f0547879bb2
Source dataset
uspto-grants-1984_07
Patent number
US04460503

Reaction notes

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