4-Methylmorpholine → 1-O-[(Z)-[amino-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]methylidene]amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate

HRID 2084485Notes

Reaction equation

HRID 2084485 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@H:8]([CH2:12][CH2:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:39]/[C:40](=[N:54]\O)/[C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][N:42]1[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]>C(Cl)Cl.O>[NH2:54]/[C:40](=[N:39]\[O:10][C:9](=[O:11])[C@@H:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])[CH2:12][CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)/[C@@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][N:42]1[C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 9835906(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acidHCID 59085902tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

Product 1

HCID 878326501-O-[(Z)-[amino-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]methylidene]amino] 4-O-tert-butyl (2R)-2-(3-cyclohexylpropyl)butanedioate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-2-(2-tert-butoxy-2-oxoethyl)-5-cyclohexylpentanoic acid (preparation 168) (500 mg, 1.67 mmol) in DCM (20 ml) was treated with HOBt (227 mg, 1.67 mmol), NMM (203 μl, 1.85 mmol) and WSCDI (354 mg, 1.85 mmol) followed by tert-butyl (2S)-2-[(Z)-amino(hydroxyimino)methyl]-1-piperidinecarboxylate (WO 9945006) (406 mg, 1.67 mmol) and stirred at room temperature, under a nitrogen atmosphere for 18 hours. H2O (10 ml) was added and after 10 minutes the reaction mixture was separated in a 5 micron filter cartridge. The solvent was removed under reduced pressure to afford the title compound as a colourless foam.

Workup

  1. customwas separated in a 5 micron
  2. filtrationfilter cartridge
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f8f690c5a5da4f41af54aad7dac52840
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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