Acetic Acid → 1-{4-[(4-tert-butylcyclohexylamino)methyl]phenyl}-2-(2H-tetrazol-5-yl)ethanol

HRID 480376Notes

Reaction equation

HRID 480376 reaction equation
[OH:1][CH:2]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[CH2:3][C:4]1[N:5]=[N:6][NH:7][N:8]=1.[C:17]([CH:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.C([BH3-])#N.[Na+]>C(Cl)Cl.C[C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O.CN(C=O)C.CO>[C:17]([CH:21]1[CH2:22][CH2:23][CH:24]([NH:27][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([CH:2]([OH:1])[CH2:3][C:4]3[N:5]=[N:6][NH:7][N:8]=3)=[CH:10][CH:11]=2)[CH2:25][CH2:26]1)([CH3:20])([CH3:18])[CH3:19]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 793964-tert-ButylcyclohexylamineHCID 5003444Sodium cyanoborohydrideHCID 187689064-[1-hydroxy-2-(2H-tetrazol-5-yl)ethyl]benzaldehyde

Product 1

HCID 187688861-{4-[(4-tert-butylcyclohexylamino)methyl]phenyl}-2-(2H-tetrazol-5-yl)ethanol

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 5488810Peptide oostatic hormoneSolvent

Procedure

Resin bound 4-[1-hydroxy-2-(2H-tetrazol-5-yl)ethyl]benzaldehyde (50 mg) was swelled in DCM for 30 min. Solvent was removed, and the resin was washed once with DMF. A solution of 4-tert-butylcyclohexyl amine (25 mg, 0.164 mmol) in 50% TMOF in DMF (1 ml,) was added followed by acetic acid (50 μl). The mixture was shaken at room temperature for 3 hours, then a solution of sodium cyanoborohydride (13 mg, 0.20 mmol) in 50% MeOH in DMF (1 ml) was added. The resin-mixture was shaken overnight at room temperature, then drained and washed with DMF (3×2 ml) and DCP (3×2 ml).

Workup

  1. customSolvent was removed
  2. washthe resin was washed once with DMF
  3. stirringThe resin-mixture was shaken overnight at room temperature
  4. washwashed with DMF (3×2 ml) and DCP (3×2 ml)

Sources & evidence

ORD record
ord-ac170a3c0e524448bab96272c0188917
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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