Dimethyl Sulfide → HCID 178482982, compound

HRID 1821456Notes

Reaction equation

HRID 1821456 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][N:14]([CH3:88])[C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][C@@H:24]([CH2:32][CH2:33][C:34](=[O:87])[NH:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][NH:53][C:54](=[O:86])[CH2:55][O:56][C:57]4[CH:62]=[CH:61][C:60]([C:63]5[NH:67][N:66]=[C:65]6[C:68]7[CH:69]=[CH:70][CH:71]=[C:72]([NH:76][C:77]([NH:79][N:80]8[CH2:85][CH2:84][O:83][CH2:82][CH2:81]8)=[O:78])[C:73]=7[C:74](=[O:75])[C:64]=56)=[CH:59][CH:58]=4)[C:25]([O:27]C(C)(C)C)=[O:26])=[O:22])=[CH:17][CH:16]=3)[N:8]=2)[N:3]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl.S(C)C>O>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][N:14]([CH3:88])[C:15]3[CH:16]=[CH:17][C:18]([C:21]([NH:23][C@@H:24]([CH2:32][CH2:33][C:34](=[O:87])[NH:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][NH:53][C:54](=[O:86])[CH2:55][O:56][C:57]4[CH:62]=[CH:61][C:60]([C:63]5[NH:67][N:66]=[C:65]6[C:68]7[CH:69]=[CH:70][CH:71]=[C:72]([NH:76][C:77]([NH:79][N:80]8[CH2:85][CH2:84][O:83][CH2:82][CH2:81]8)=[O:78])[C:73]=7[C:74](=[O:75])[C:64]=56)=[CH:59][CH:58]=4)[C:25]([OH:27])=[O:26])=[O:22])=[CH:19][CH:20]=3)[N:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178482983HCID 178482983, compound

Product 1

HCID 178482982HCID 178482982, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 30 (0.45 g, 0.37 mmol) was treated with 20 ml of a cleavage cocktail (10:10:1:1 TFA:CH2Cl2: Me2S: H2O). After one hour, the solvent was removed and the residue purified by RPHPLC. Fractions containing the product were combined, concentrated to a small volume and lyophilized to yield a yellow solid (0.23 g, 0.18 mmol, 49%, compound 32).

Workup

  1. customthe solvent was removed
  2. customthe residue purified by RPHPLC
  3. additionFractions containing the product
  4. concentrationconcentrated to a small volume

Sources & evidence

ORD record
ord-6d7964baaf0e45b1ab3cc37da22317a8
Source dataset
uspto-grants-2009_10
Patent number
US07605175B2

Reaction notes

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