Acetic Acid → HCID 178456041, compound

HRID 2092384Notes

Reaction equation

HRID 2092384 reaction equation
[C@H:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][C:11](=[O:41])[N:12]([C:23]3[CH:28]=[CH:27][C:26]([N:29]([CH2:31][C@H:32]4[CH2:37][CH2:36][C@H:35]([NH:38][CH2:39][CH3:40])[CH2:34][CH2:33]4)[CH3:30])=[CH:25][CH:24]=3)[CH:13]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:8][C:7]=1[O:42][CH3:43])([CH2:3][CH3:4])[CH3:2].[CH3:44]C(O)=O.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC#N>[C@H:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][C:11](=[O:41])[N:12]([C:23]3[CH:28]=[CH:27][C:26]([N:29]([CH2:31][C@H:32]4[CH2:33][CH2:34][C@H:35]([N:38]([CH2:39][CH3:40])[CH3:44])[CH2:36][CH2:37]4)[CH3:30])=[CH:25][CH:24]=3)[CH:13]2[C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:8][C:7]=1[O:42][CH3:43])([CH2:3][CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178464520HCID 178464520, compound

Product 1

HCID 178456041HCID 178456041, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 52 (13.8 mg, 0.023 mmol) in MeCN (0.5 ml) were successively added AcOH (0.003 ml, 0.046 mmol), formaldehyde (37% in water, 0.003 ml, 0.046 mmol) and NaBH(OAc)3 (9.7 mg, 0.046 mmol) at RT. The reaction mixture was stirred at RT for 2 h then directly subjected to purification by reverse phase prep-HPLC (Waters system) to yield the title compound (TFA salt, 7.4 mg, 0.010 mmol, 44%) as a colorless solid. HPLC: AtRet=2.01 min; LC-MS: m/z 618.4 [M+H]+.

Workup

  1. customat RT
  2. customthen directly subjected to purification by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-10c82ac92b7b40c0b328c4119fd4308b
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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