Citric Acid → HCID 66925750, compound

HRID 1944110Notes

Reaction equation

HRID 1944110 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)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.C(O)(=O)[CH2:52][C:53]([CH2:58][C:59](O)=O)([C:55]([OH:57])=O)[OH:54]>ClCCl>[C:11]([O:10][C:8]([N:1]1[CH2:7][CH2:6][CH2:5][N:4]([C:55]([C:53]2([OH:54])[CH2:52][CH2:59][CH2:58]2)=[O:57])[CH2:3][CH2:2]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 66925750HCID 66925750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of example 10a (340 mg), tert-butyl 1,4-diazepane-1-carboxylate (694 μl), DIPEA (2.4 ml) and BOP (1.9 g) in dichloromethane (15 ml) was stirred for 18 h at room temperature. The reaction mixture was poured into an aqueous citric acid solution (5%) and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in toluene/acetone [1/0→7/3 (v/v)] as eluent.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel in toluene/acetone [1/0→7/3 (v/v)] as eluent

Sources & evidence

ORD record
ord-0a3bdfd907da4a2a80c17ef8ae1a9cb2
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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