Acetylcysteamine → HCID 86740287, compound

HRID 1719334Notes

Reaction equation

HRID 1719334 reaction equation
O=[C:2]1[CH2:8][C@H:7]2[N:4]([C:5](=[O:26])[C@H:6]2[C:9]([CH3:25])([O:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])[CH3:10])[C@H:3]1[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28].C(N(C(C)C)CC)(C)C.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[SH:66][CH2:67][CH2:68][NH:69][C:70](=[O:72])[CH3:71]>CN(C1C=CN=CC=1)C.C(#N)C.C(OCC)(=O)C>[C:70]([NH:69][CH2:68][CH2:67][S:66][C:2]1[CH2:8][C@H:7]2[N:4]([C:5](=[O:26])[C@H:6]2[C:9]([CH3:10])([O:11][C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[O:13])[CH3:25])[C:3]=1[C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=1)=[O:28])(=[O:72])[CH3:71]

Participants

8

Reactant 4

HCID 14484AcetylcysteamineHCID 75654Diphenyl chlorophosphateHCID 81531Diisopropylethylamine2×HCID 185992114-nitrobenzyl (2R,5R,6R)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 86740287HCID 86740287, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent5×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-nitrobenzyl (2R,5R,6R)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]heptane-2-carboxylate (58 mg) and 4-(N,N-dimethylamino)pyridine (1.3 mg) in acetonitrile (3 ml) was added a solution of diisopropylethylamine (22.4 μl) in acetonitrile (0.21 ml) at 0° C. To the mixture was added a solution of diphenyl chlorophosphate (23.3 μl) in acetonitrile (0.21 ml) at 0° C. After stirring at 0° C. for 1.5 hours, the reaction mixture was cooled to -15° C., to which a solution of diisopropylethylamine (74.6 μl) in acetonitrile (0.73 ml) was added. To the mixture was added a solution of N-(2-mercaptoethyl)acetamide (13.4 mg) in acetonitrile (0.12 ml). After standing overnight at -15° C., the mixture was diluted with ethyl acetate (50 ml), washed in turn with water and saturated aqueous sodium chloride, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (2 g) eluting with a mixture of methylene chloride and acetone (20:1 to 2:1) to give 4-nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (56 mg) as an amorphous solid.

Workup

  1. additionwas added
  2. waitAfter standing overnight at -15° C.
  3. washwashed in turn with water and saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (2 g)
  7. washeluting with a mixture of methylene chloride and acetone (20:1 to 2:1)

Sources & evidence

ORD record
ord-c13329a6bd994713a5971e37ebe60b7d
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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