Diisopropylethylamine → HCID 141603155, compound

HRID 494032Notes

Reaction equation

HRID 494032 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 12082687HCID 12082687, compound

Product 1

HCID 141603155HCID 141603155, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Compound 13 (1.00 g, 3.16 mmol), N,N′-bis-(tert.-butoxycarbonyl)-S-methylisothiourea (1.00 g, 3.44 mmol) and N-ethyldiisopropylamine (0.60 ml, 3.44 mmol) in absolute N,N-dimethylformamide (60 ml) was mixed with silver nitrate (0.55 g, 3.24 mmol) and the mixture stirred for 1.5 h. Then the silver mercaptane was filtered off through Celite and washed afterwards with CH2Cl2 (4×50 ml). The filtrate was washed with H2O (6×200 ml) and saturated NaCl solution (1×200 ml), dried (Na2SO4) and evaporated. In this way 1.85 g of a yellow oil were obtained which was purified through MPLC (p=5 bar, silica gel 60, CH2Cl2/MeOH 10:1). Yield: 0.67 g (38%) of white foam resin: 1H-NMR (CDCl3): δ 11.53 (s, br, NH—COO(CH3)3); 8.81 (d, J=8.0, C(6)-NH—); 6.73 (d, J=8.2,1 arom. H); 6.56 (d, J=8.2, 1 arom. H); 4.66 (dd, 3J=2.6, 4J=1.6, H—C(5)); 3.25 (s, CH3O—C(14)); 2.35 (s, CH3N); 1.50 (s, 2×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 (6×200 ml) and saturated NaCl solution (1×200 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5f14bff3a0f447699f7ceac770bbd1b1
Source dataset
uspto-grants-2009_05
Patent number
US07538118B2

Reaction notes

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