Dichloromethane → HCID 136359216, compound

HRID 1819374Notes

Reaction equation

HRID 1819374 reaction equation
C(OC([N:8]1[CH:17]([CH:18]([OH:47])[CH:19]([O:21][C:22](=[O:46])[CH2:23][CH2:24][CH:25]([NH:38]C(OC(C)(C)C)=O)[C:26](=[O:37])[NH:27][CH:28]([C:30]([O:32]C(C)(C)C)=[O:31])[CH3:29])[CH3:20])[CH2:16][NH:15][C:14]2[NH:13][C:12]([NH2:48])=[N:11][C:10](=[O:49])[C:9]1=2)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:58]>>[ClH:58].[ClH:58].[NH2:48][C:12]1[NH:11][C:10](=[O:49])[C:9]2[NH:8][CH:17]([CH:18]([OH:47])[CH:19]([O:21][C:22](=[O:46])[CH2:23][CH2:24][CH:25]([NH2:38])[C:26](=[O:37])[NH:27][CH:28]([C:30]([OH:32])=[O:31])[CH3:29])[CH3:20])[CH2:16][NH:15][C:14]=2[N:13]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178465110HCID 178465110, compound

Product 1

HCID 136359216HCID 136359216, compoundYield 98%

Procedure

The product of step b) (0.048 g, 0.07 mmol) was treated with trifluoroacetic acid (1 ml, 27 mmol) in 1 ml of DCM. The mixture was stirred at room temperature under an atmosphere of nitrogen for 2 h. The product was precipitated by the addition of 20 ml of diethyl ether. The product was filtered and dried in a nitrogen purged vacuum oven to give the title compound as a white solid (0.051 g, 98%). 1H NMR (CD3OD) δ 4.45-4.39 (m, 2H), 4.23-4.20 (m, 2H), 3.94 (t, J=6.3 Hz, 1H), 2.60-2.55 (m, 2H), 2.49-2.24 (m, 2H), 2.17-2.12 (m, 3H), 1.45 (dd, J=7.4 Hz, J=9.7 Hz, 6H). MS: ESI (positive): 442 (M+H).

Workup

  1. customThe product was precipitated by the addition of 20 ml of diethyl ether
  2. filtrationThe product was filtered
  3. customdried in a nitrogen
  4. custompurged vacuum oven

Sources & evidence

ORD record
ord-510502f453424b1aaf5af3212ca6f49d
Source dataset
uspto-grants-2009_10
Patent number
US07601717B2

Reaction notes

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