2-Amino-2-methyl-1,3-propanediol → HCID 19076617, compound

HRID 234544Notes

Reaction equation

HRID 234544 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[C:13](=[O:28])[C:12]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[NH:29][CH2:30][CH3:31].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23](=[O:24])[NH:1][C:2]([CH2:5][OH:6])([CH2:3][OH:4])[CH3:7])=[CH:26][CH:27]=1)[C:13](=[O:28])[C:12]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[NH:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19076468HCID 19076468, compound

Product 1

HCID 19076617HCID 19076617, compoundYield 40.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.172 g of 2-amino-2-methylpropane-1,3-diol in 2 ml of DMF is added at RT to a mixture of 0.374 g of the compound obtained in step B of EXAMPLE 241, 0.25 g of triethylamine, 0.364 g of BOP and 5 ml of DCM and the reaction mixture is stirred for 3 hours at RT. It is concentrated under vacuum, the residue is taken up with water and extracted with AcOEt, the organic phase is washed twice with a 5% solution of potassium carbonate, with water 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 an AcOEt/DCM mixture (80/20; v/v) as the eluent to give 0.18 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=138°-141° C.

Workup

  1. concentrationIt is concentrated under vacuum
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed twice with a 5% solution of potassium carbonate, with water and with a saturated solution of NaCl
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using an AcOEt/DCM mixture (80/20; v/v) as the eluent

Sources & evidence

ORD record
ord-981bfd442d5c4f55bc71cb34de7051e8
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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