Formaldehyde → HCID 131732132, compound

HRID 1399498Notes

Reaction equation

HRID 1399498 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C=O.[BH3-][C:45]#N.[Na+]>CC#N.O>[C:1]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][S:22][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:18])[CH3:45])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131732131HCID 131732131, compound

Product 1

HCID 131732132HCID 131732132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Boc-NH—(CH2)2—NH—(CH2)5—CONH—(CH2)2-STrt (189 mg, 0.27 mmol) and HCHO (35% aqueous, 113 μl) were dissolved in MeCN (1.5 ml) and NaCNBH3 (34 mg, 0.54 mmol) was added. The reaction mixture was stirred for 5 h at RT. After completion of the reaction (MS) the solution was diluted with H2O (5 ml) and extracted with CH2Cl2 (3×5 ml). The combined organic layers were dried over MgSO4, filtered and the solvent was removed in vacuo. The residue was purified by RP-HPLC to get Boc-NH—(CH2)2—N(CH3)—(CH2)5—CONH—(CH2)2-STrt.

Workup

  1. customAfter completion of the reaction (MS) the solution
  2. extractionextracted with CH2Cl2 (3×5 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-121d4e470a7e4f27a0c2fd59d3451176
Source dataset
uspto-grants-2014_12
Patent number
US08906847B2

Reaction notes

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