Tetrahydro-4H-pyran-4-one → HCID 86636658, compound

HRID 1361339Notes

Reaction equation

HRID 1361339 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([N:8]([C:20]([CH:22]2[CH2:26][CH2:25][CH2:24][O:23]2)=[O:21])[C@@H:9]2[CH2:13][NH:12][C@H:11]([C:14]([N:16]([CH2:18][CH3:19])[CH3:17])=[O:15])[CH2:10]2)[CH2:4][CH2:3]1.C(O[C:33]([N:35]1[CH2:39][C@@H:38]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)[C@H:37]([C:47]([OH:49])=O)[CH2:36]1)=O)(C)(C)C.[O:50]1[CH2:55][CH2:54]C(=O)[CH2:52][CH2:51]1>>[ClH:46].[Cl:46][C:43]1[CH:42]=[CH:41][C:40]([C@@H:38]2[CH2:39][N:35]([CH:33]3[CH2:54][CH2:55][O:50][CH2:51][CH2:52]3)[CH2:36][C@H:37]2[C:47]([N:12]2[CH2:13][C@@H:9]([N:8]([CH:5]3[CH2:6][CH2:7][C:2]([CH3:1])([CH3:27])[CH2:3][CH2:4]3)[C:20]([C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[O:21])[CH2:10][C@H:11]2[C:14]([N:16]([CH2:18][CH3:19])[CH3:17])=[O:15])=[O:49])=[CH:45][CH:44]=1

Participants

4

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 27621121-(tert-Butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acidHCID 66971291HCID 66971291, compound

Product 1

HCID 86636658HCID 86636658, compoundYield 80%

Procedure

(4S)-4-[(4,4-dimethylcyclohexyl)(tetrahydrofuran-2-ylcarbonyl)amino]-N-ethyl-N-m ethyl-L-prolineamide (100 mg, 0.26 mmol) prepared in Step D of Example A2 and (3S,4R)-1-(tert-butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid prepared in Preparation Example A9-9 were reacted according to the procedure described in Step F of Example A1, and then according to that in Step E of Example A1. This compound was reacted with tetrahydro-4H-pyran-4-one via reductive amination as described in Step A of Example A1, and purified by HPLC. This TFA salt of the compound was treated according to the procedure described in Step G of Example A1 to give the title compound (139 mg, 80%).

Workup

  1. customwere reacted
  2. custompurified by HPLC
  3. additionThis TFA salt of the compound was treated

Sources & evidence

ORD record
ord-4f3457dbf33548b790454d9354bca2aa
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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