Triethylamine → HCID 19076385, compound

HRID 234543Notes

Reaction equation

HRID 234543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)[C:6](=[O:21])[C:5]2([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[NH:22][CH2:23][CH3:24].C(N(CC)CC)C.[NH2:39][C:40]([CH3:44])([CH3:43])[CH2:41][OH:42].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](=[O:18])[NH:39][C:40]([CH3:44])([CH3:43])[CH2:41][OH:42])=[CH:14][CH:13]=1)[C:6](=[O:21])[C:5]2([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[NH:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19076468HCID 19076468, compound

Product 1

HCID 19076385HCID 19076385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.374 g of the compound obtained in step B of EXAMPLE 241 in 5 ml of DCM is cooled to 0° C. and 0.34 ml of triethylamine and then 0.16 ml of 2-amino-2-methylpropan-1-ol and 0.364 g of BOP are added. The reaction mixture is stirred for 1 hour at RT and concentrated under vacuum. The residue is taken up with AcOEt, the organic phase is washed with water, with a 5% solution of potassium carbonate and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/AcOEt mixture (70/30; v/v) as the eluent to give 0.3 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=170°-172° C.

Workup

  1. concentrationconcentrated under vacuum
  2. washthe organic phase is washed with water, with a 5% solution of potassium carbonate and with a saturated solution of NaCl
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-f69039fddf3e429cafda0e2b1c901599
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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