Diisopropylethylamine → HCID 141603152, compound

HRID 494030Notes

Reaction equation

HRID 494030 reaction equation
N[C@@H:2]1[CH2:15][CH2:14][C@:13]2([O:16][CH3:17])[C@:4]34[CH2:20][CH2:19][N:18]([CH3:21])[C@@H:12]2[CH2:11][C:10]2[CH:9]=[CH:8][C:7]([OH:22])=[C:6]([O:23][C@@H:3]13)[C:5]4=2.[C:24]([O:28][C:29]([NH:31][C:32](=[N:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])SC)=[O:30])([CH3:27])([CH3:26])[CH3:25].C([N:45](C(C)C)C(C)C)C>CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[O:23]1[C@@H:3]2[C@@:4]34[CH2:20][CH2:19][N:18]([CH3:21])[C@@H:12]([C@:13]3([O:16][CH3:17])[CH2:14][CH2:15][C@H:2]2[N:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:32]([NH:31][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])=[NH:45])[CH2:11][C:10]2=[C:5]4[C:6]1=[C:7]([OH:22])[CH:8]=[CH:9]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 12082689HCID 12082689, compound

Product 1

HCID 141603152HCID 141603152, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 15 (0.94 g, 2.97 mmol), N,N′-bis-(tert.-butoxycarbonyl)-S-methylisothiourea (0.92 g, 3.17 mmol) and N-ethyldiisopropylamine (0.58 ml, 3.33 mmol) in absolute N,N-dimethylformamide (40 ml) was mixed with silver nitrate (0.54 g, 3.18 mmol) and the mixture stirred for 4 hours. Then the silver mercaptane was filtered off through Celite and washed afterwards with CH2Cl2 (4×50 ml). The filtrate was washed with H2O (10×150 ml) and saturated NaCl solution (2×150 ml), dried (Na2SO4) and evaporated. In this way 1.46 g of a yellow foam resin was obtained which was purified through MPLC (p=5 bar, silica gel 60, CH2Cl2/MeOH/conc. ammonia 95:4, 5:0.5). Yield: 0.77 g (46%) of green foam resin: 1H-NMR (CDCl3): δ 11.49 (s, br, NH—COO(CH3)3); 8.59 (d, J=8.0, C(6)-NH—); 6.71 (d, J=8.4, 1 arom. H); 6.56 (d, J=8.4, 1 arom. H); 4.41 (d, J=7.2, H—C(5)); 3.22 (s, CH3O—C(14)); 2.38 (s, CH3N); 1.51 (s, C(CH3)3), 1.47 (s, C(CH3)3).

Workup

  1. filtrationThen the silver mercaptane was filtered off through Celite
  2. washwashed afterwards with CH2Cl2 (4×50 ml)
  3. washThe filtrate was washed with H2O (10×150 ml) and saturated NaCl solution (2×150 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-63809c361bfc40a6aad729f63d86628d
Source dataset
uspto-grants-2009_05
Patent number
US07538118B2

Reaction notes

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