Hydrochloric Acid → HCID 11306208, compound

HRID 353264Notes

Reaction equation

HRID 353264 reaction equation
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[N+](C1C=C(Cl)C(Cl)=CC=1C[C:28]([N:30](C)[C@@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=2)CC[C@H:32]1[N:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1)=O)([O-])=O.[C:50]([NH:57][C:58]1[CH:63]=[CH:62][C:61]([CH2:64][C:65]([OH:67])=O)=[CH:60][CH:59]=1)([O:52][C:53]([CH3:56])(C)C)=[O:51].N1C=CC=CC=1.Cl>O>[CH2:53]([O:52][C:50]([NH:57][C:58]1[CH:59]=[CH:60][C:61]([CH2:64][C:65]([N:30]([CH3:28])[C@@H:31]([C:40]2[CH:35]=[CH:36][CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=2)[CH2:32][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:67])=[CH:62][CH:63]=1)=[O:51])[CH2:56][CH2:1][CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868Dicyclohexylcarbodiimide2×HCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 228794362-(2-Nitro-4,5-dichlorophenyl)-N-methyl-N-[(+/-)-trans-2-(1-pyrrolidinyl)-7-nitro-1,2,3,4-tetrahydronaphth-1-yl]acetamide

Product 1

HCID 11306208HCID 11306208, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared via the general DCC/pyr coupling method from 8 (1.9948 g, 8.001 mmol), N-Boc-4-aminophenylacetic acid (3.0589 g, 12.173 mmol), DCC(2.6602 g, 12.89 mmol), and pyridine (1.04 mL, 12.9 mmol). The crude product was gravity column chromatographed eluting with CH2Cl2:2% NH3:1% MeOH before it was converted to the HCl salt with 1.0 M HCl in Et2O and crystallized from MeOH to yield 18HCl.(0.4891 g, 12%, first crop): m.p. (HCl salt) 170° C. (dec); 1H NMR (HCl salt, DMSO-d6) δ1.49 (s, 9H, t-butyl), 2.01 (br s, 4H, —CH2CH2—), 2.83 (s, 3H, —NCH3), 3.1-4.15 (complex, 8H, 4 —CH2—), 6.27 (m, 1H, —CH—), 7.17 (d, J=8 Hz, 2H, aromatic), 7.39 (d, J=8 Hz, 2H, aromatic), 7.7 (m, 2H, aromatic), 8.09 (s, 1H, aromatic), 8.23 (d, J=6 Hz, 1H, aromatic), 9.3 (s, 1H, —NHBoc). MS(FAB) 483. Anal. (C, H, N) C26H34N4O5HCl.0.25 H2O.

Workup

  1. customchromatographed
  2. washeluting with CH2Cl2
  3. customcrystallized from MeOH
  4. customto yield 18HCl

Sources & evidence

ORD record
ord-3e6b5e09a09943ecbdf0fec0cf143e21
Source dataset
uspto-grants-2004_06
Patent number
US06750216B2

Reaction notes

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