Trifluoroacetic acid methylene chloride → (6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

HRID 481242Notes

Reaction equation

HRID 481242 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]2[C@H:19]([C:22]([O:24]C(C)(C)C)=[O:23])[CH2:20][CH2:21][C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:17](=[O:18])[N:16]2[C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21][C:15]2=[N:14][CH:13]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 54224046tert-Butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylate

Product 1

HCID 53717804(6S)-3-{[(Benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl ester 1h (11.13 g, 28.9 mmol) was dissloved in 1:1 CH2Cl2/TFA. 1 mL H2O was added and the mixture was stirred overnight at rt. The mixture was concentrated and the resultant residue was co-evaporated with CCl4 (3×). The residual oil was triturated with 1:1 Et2O/hexanes (100 mL) and the solid (9.0 g, 95%) was collected and dried, to provide 1i. 1H NMR (300 MHz, CDCl3) δ8.69 (br s, 1H), MS (ESI) 330.3 (M+H+); 328.3 (M−H+).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residual oil was triturated with 1:1 Et2O/hexanes (100 mL)
  3. customthe solid (9.0 g, 95%) was collected
  4. customdried

Sources & evidence

ORD record
ord-758bc9327ec14cef9c424391efb96bf5
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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