2-Naphthalenecarboxaldehyde → HCID 15390990, compound

HRID 342115Notes

Reaction equation

HRID 342115 reaction equation
[NH2:1][CH:2]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH2:6][C@@H:5]1[CH2:22][CH2:23][CH2:24][CH3:25].[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[CH:45]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:31]([O:30][C:28]([NH:27][CH2:26][CH:2]([NH:1][CH2:45][C:36]1[CH:37]=[CH:38][C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:35]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH2:6][C@@H:5]1[CH2:22][CH2:23][CH2:24][CH3:25])=[O:29])([CH3:33])([CH3:32])[CH3:34]

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86753518HCID 86753518, compound

Product 1

HCID 15390990HCID 15390990, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1, Step D except using 1-[(2-amino-3-tert-butoxycarbonylaminoprop-1-yl]-2(S)-butyl-4-(1-naphthoyl)piperazine (0.287 g, 0.613 mmol), naphthalene-2-carboxaldehyde (0.95 g, 0.613 mmol), sodium triacetoxyborohydride (0.194 g, 0.919 mmol), in dichloroethane (15 mL) at pH 6. The crude product was chromatographed on silica gel with 5% methanol in chloroform (Rf 0.30), and the title compound isolated as a foam. FAB ms (m+1) 609.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel with 5% methanol in chloroform (Rf 0.30)

Sources & evidence

ORD record
ord-447dae62d8dd429382c4ac8d96297c41
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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