1,2-Dichloroethane → HCID 23587442, compound

HRID 489666Notes

Reaction equation

HRID 489666 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34](OC(C)(C)C)=[O:35])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:62]([N:69]1[CH:72](C(O)=O)[CH2:71][CH2:70]1)([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33][C:34]([CH:71]2[CH2:70][N:69]([C:62]([O:64][C:65]([CH3:66])([CH3:67])[CH3:68])=[O:63])[CH2:72]2)=[O:35])[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[S:25]([CH3:28])(=[O:27])=[O:26])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 36238861-[(Tert-butoxy)carbonyl]azetidine-2-carboxylic acidHCID 23587431HCID 23587431, compound

Product 1

HCID 23587442HCID 23587442, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in Example 11 (Step c) using N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl](tert-butoxy)carboxamide (Example 11 Step b) (450 mg, 0.76 mmol) and 50% TFA in CH2Cl2 (6 mL) followed by EDC (Aldrich) (259 mg, 1.35 mmol), HOBT (Aldrich) (270 mg, 2.0 mmol) and N-Boc-azetidine-4-carboxylic acid (PepTech Corporation) (220 mg, 1.1 mmol) in THF (20 mL). Purification by silica gel chromatography (10:25:65 MeOH:EtOAc:hexane) provided the title compound as a white foam (365 mg). MS (ESI, pos. ion) m/z: 673 (M+1); (ESI, neg. ion) m/z: 671 (M−1). Calc'd for C34H45ClN4O6S: 673.26.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (10:25:65 MeOH:EtOAc:hexane)

Sources & evidence

ORD record
ord-8746b430bf9f4b8f81ac8b0fbb41dda6
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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