Formaldehyde → HCID 178486518, compound

HRID 2092396Notes

Reaction equation

HRID 2092396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=3)[CH2:11][C:10](=[O:24])[N:9]2[C:25]2[CH:26]=[CH:27][C:28]([N:31]([CH2:33][C@H:34]3[CH2:39][CH2:38][C@H:37]([NH:40][CH2:41][C:42]([NH:44][CH:45]([CH3:47])[CH3:46])=[O:43])[CH2:36][CH2:35]3)[CH3:32])=[N:29][CH:30]=2)=[CH:4][CH:3]=1.[CH2:48]=O>CC(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH:19]([CH3:20])[CH3:21])[CH:16]=3)[CH2:11][C:10](=[O:24])[N:9]2[C:25]2[CH:30]=[N:29][C:28]([N:31]([CH2:33][C@H:34]3[CH2:35][CH2:36][C@H:37]([N:40]4[CH2:41][C:42](=[O:43])[N:44]([CH:45]([CH3:47])[CH3:46])[CH2:48]4)[CH2:38][CH2:39]3)[CH3:32])=[CH:27][CH:26]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 178486519HCID 178486519, compound

Product 1

HCID 178486518HCID 178486518, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The mixture of Example 131 (80 mg, 0.121 mmol) and formaldehyde (0.090 mL, 37% solution, 10 eq., 1.208 mmol) was heated for 5 h in 2-propanol (4 mL) at 85° C. The mixture was concentrated to dryness and the residue was purified by reversed phase column chromatography. The fractions containing the product were pooled and worked up (addition of NaHCO3), yielding the title compound as an off-white solid (46 mg, 0.068 mmol, >98%). HPLC: HtRet=1.40 min; LC-MS: m/z 674.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was purified by reversed phase column chromatography
  3. additionThe fractions containing the product
  4. addition(addition of NaHCO3)

Sources & evidence

ORD record
ord-7da46cc587da440fa1e48ef4d91e6e3b
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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