1,2-Dichloroethane → HCID 69151551, compound

HRID 489651Notes

Reaction equation

HRID 489651 reaction equation
[NH2:1][C@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:7][CH2:6]1)=[O:4].CCN(C(C)C)C(C)C.[C:39]([NH:46][C@@H:47]1[CH2:51][CH2:50][C@H:49]([C:52](O)=[O:53])[CH2:48]1)([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:2]([NH:1][C:52]([C@@H:49]2[CH2:50][CH2:51][C@H:47]([NH:46][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:48]2)=[O:53])[C:3]([N:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH2:7][CH2:6]2)=[O:4])=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 1512529(1S,3R)-3-(((tert-butoxy)carbonyl)amino)cyclopentane-1-carboxylic acidHCID 69140350HCID 69140350, compound

Product 1

HCID 69151551HCID 69151551, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1, Step (f) using (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)-amino]phenyl}piperidyl)propan-1-one (Example 1, Step g) (471 mg, 1.0 mmol), DIEA (Aldrich) (0.20 mL, 1.0 mmol), (+)-(1R, 3S)—N-Boc-aminocyclopentane-3-carboxylic acid (PepTech Corporation) (344 mg, 1.5 mmol), HOAT (Aldrich) (232 mg, 1.70 mmol) and EDC (Aldrich) (544, 2.84 mmol) in DMF (10 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (421 mg). MS (ESI, pos. ion) m/z: 647 (M+1); MS (ESI, neg ion) m/z: 645 (M−1). Calc'd for C32H43ClN4O6S: 647.23.

Workup

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

Sources & evidence

ORD record
ord-533c44926e8d4aa8a9526e9fb25f6eb6
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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