Trifluoroacetic acid → HCID 10227132, compound

HRID 1058249Notes

Reaction equation

HRID 1058249 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][CH:9]([CH:44]([F:46])[F:45])[CH2:10][C:11]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:12]=1[CH2:13][NH:14][C:15](=[O:38])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21](=[O:37])[C@H:22]([NH:29]C(OC(C)(C)C)=O)[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[NH2:29][C@H:22]([CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1)[C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:15]([NH:14][CH2:13][C:12]1[CH:39]=[C:40]([Cl:43])[CH:41]=[CH:42][C:11]=1[CH2:10][CH:9]([NH2:8])[CH:44]([F:46])[F:45])=[O:38])=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69939192HCID 69939192, compound

Product 1

HCID 10227132HCID 10227132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.65 mL) was added to a stirred solution of N-[2-(2-amino-3,3-difluoropropyl)-5-chlorobenzyl]-1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-prolinamide (0.080 g, 0.14 mmol) in CH2Cl2 (0.7 mL). After 1 h the solvent was evaporated in vacuo and the residue was partitioned between EtOAc and saturated aqueous Na2CO3. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was partitioned between EtOAc and 1M HCl. The aqueous layer was evaporated in vacuo to give the HCl salt of the title compound as an off white solid; MS m/z=471.5.

Workup

  1. customAfter 1 h the solvent was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous Na2CO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was partitioned between EtOAc and 1M HCl
  6. customThe aqueous layer was evaporated in vacuo

Sources & evidence

ORD record
ord-1fc4fae9926549668c7345ad52851c18
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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