1,2-Dichloroethane → HCID 131725244, compound

HRID 489689Notes

Reaction equation

HRID 489689 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23]C(C)(C)C)=O)[CH2:17][CH2:16]1)=[O:7].C(O)(C(F)(F)F)=O.[NH:37]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@@H:38](C(O)=O)[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][C@@H:38]([NH:37][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:21](=[O:23])[N:18]2[CH2:17][CH2:16][CH:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]3[CH:3]=[CH:4][NH:5][C:6]3=[O:7])[CH2:20][CH2:19]2)=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acid2×HCID 757711-HydroxybenzotriazoleHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 22266258HCID 22266258, compound

Product 1

HCID 131725244HCID 131725244, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 17 (Step b) using tert-butyl 4-(2-{[(2,2-dimethoxyethyl)amino]carbonylamino}phenyl)piperidine-carboxylate (Step a) (0.742 g, 1.82 mmol) and a 50% aqueous TFA soln (20 mL) followed by Boc-p-Cl-D-PheOH (Advanced ChemTech) (0.545 g, 1.82 mmol), EDC (Advanced ChemTech) (0.523 g, 2.73 mmol), HOBT (Novabiochem) (0.246 g, 1.82 mmol) and TFA (Aldrich) (0.25 mL, 1.82 mmol) in CH2Cl2 (10 mL). Purification by silica gel chromatography (100% EtOAc then 1:9 MeOH:EtOAc) provided the title compound as a white solid (0.675 g). MS (ESI, pos. ion) m/z: 525 (M+1). Calc'd for C28H33ClN4O4: 524.22.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (100% EtOAc

Sources & evidence

ORD record
ord-2ff4db042ac14bd8b26fee42e2ff7da8
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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