Trifluoroacetic acid → HCID 67111566, compound

HRID 1177620Notes

Reaction equation

HRID 1177620 reaction equation
C(OC([NH:8][CH:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][C:23]3[C:28]([N:29]=2)=[CH:27][CH:26]=[C:25]([C:30]2([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:32][CH2:31]2)[N:24]=3)=[C:17]([F:39])[CH:16]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.C(OC(C(CCC1C=CC(C2SC3C(N=2)=CC=C(C2(C4C=CC=CC=4)CC2)N=3)=C(F)C=1)C(O)=O)=O)(C)(C)C.[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81]>C(Cl)Cl>[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81].[NH2:8][C@H:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][C:23]3[C:28]([N:29]=2)=[CH:27][CH:26]=[C:25]([C:30]2([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:32][CH2:31]2)[N:24]=3)=[C:17]([F:39])[CH:16]=1)[C:10]([OH:12])=[O:11].[F:78][C:79]([F:84])([F:83])[C:80]([OH:82])=[O:81].[NH2:8][C@@H:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][C:23]3[C:28]([N:29]=2)=[CH:27][CH:26]=[C:25]([C:30]2([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:32][CH2:31]2)[N:24]=3)=[C:17]([F:39])[CH:16]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67111977HCID 67111977, compoundHCID 67112045HCID 67112045, compound

Product 2

HCID 67111566HCID 67111566, compoundHCID 67112873HCID 67112873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Separately, the enantiomers of 2-(tert-butoxycarbonylamino)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid were processed by the following procedure: 2-(tert-butoxycarbonyl)-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid (0.047 g, 0.086 mmol) in DCM (2.0 mL) was added trifluoroacetic acid (1.0 mL, 13 mmol). After 5 min, the solvent was removed, the solid rinsed with water and diethyl ether to give both (R)-2-amino-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid trifluoroacetic acid salt and (S)-2-amino-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)butanoic acid trifluoroacetic acid salt. MS (ESI) m/z: calculated: 447.1; Observed: 448.1 (M++1).

Workup

  1. customthe solvent was removed
  2. washthe solid rinsed with water and diethyl ether

Sources & evidence

ORD record
ord-bdc70a8db66243feb16edd8c10d5fc05
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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