Trifluoroacetic acid → HCID 59745530, compound

HRID 2080541Notes

Reaction equation

HRID 2080541 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]2[CH2:12][C@@H:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:14](C(OC(C)(C)C)=O)[C@H:8]2[CH2:7]1)=[O:5].C(O)(C(F)(F)F)=O.CCOC(C)=O.C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[CH3:1][CH:2]([CH3:27])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]2[CH2:12][C@@H:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:14][C@H:8]2[CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 59745538HCID 59745538, compound

Product 1

HCID 59745530HCID 59745530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution was made of 1-tert-butyl 2-ethyl rel-(2S,3aS,7aR)-6-(3-methyl butanoyl)octahydro-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate obtained under step a) (0.335 mmol) in DCM (2.5 mL), to which TFA (2.5 mL) was added. The reaction was left to stir for 1 hour after which time it was checked by TLC (60% EtOAc in heptanes). If the reaction had not gone to completion after this time it was left stirring and checked after every additional ½. Generally this took 2 hours. When the reaction had gone to completion the TFA/DCM was removed in vacuo before being placed on a high vacuum line for 2 hours. The product was used in the next step with no further purification.

Workup

  1. waitThe reaction was left
  2. waitwas left
  3. stirringstirring
  4. waitGenerally this took 2 hours
  5. customwas removed in vacuo
  6. waitbefore being placed on a high vacuum line for 2 hours
  7. customThe product was used in the next step with no further purification

Sources & evidence

ORD record
ord-4959502eb9be4d6abce972776ccdd161
Source dataset
uspto-grants-2011_04
Patent number
US07932389B2

Reaction notes

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