Flurenol → 9-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester

HRID 857728

Reaction equation

HRID 857728 reaction equation
[OH:1][C:2]1([C:15](O)=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[CH2:43]([O:50][C:51](=[O:57])[C@@H:52]1[CH2:56][CH2:55][CH2:54][NH:53]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:43]([O:50][C:51](=[O:57])[C@@H:52]1[CH2:56][CH2:55][CH2:54][N:53]1[C:15]([C:2]1([OH:1])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:16])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 10087FlurenolHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 590381919-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9-hydroxy-9-fluorene carboxylic acid (5.04 g, 22.3 mmol) in N,N-dimethylformamide (30 mL), cooled to 0° C. under nitrogen, was added (O-7-azabenzotriazol-1-y)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU), (9.32 g, 24.5 mmol), L-proline-benzyl ester hydrochloride (5.93 g, 24.5 mmol), and N,N-diisopropylethylamine (8.5 mL, 48.8 mmol). The mixture was stirred at 0° C. for 3 hours, then concentrated and purified on silica gel (ethyl acetate-hexane, 1:2) to give 9-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester. HPLC=96%, R.T.=3.7 min; Mass spec.(electrospray) M+1=414.1.

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel (ethyl acetate-hexane, 1:2)

Sources & evidence

ORD record
ord-d59a48e8a16546be834b83dc63975ec9
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Linked notes

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