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Triethylamine → HCID 513937, compound

HRID 987951
Notes
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Reaction equation

HRID 987951 reaction equation
[NH2:1][C@@H:2]([CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][CH2:6][CH2:7][CH2:8][C@H:9]([N:12]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][OH:11])=[O:4].C(N(CC)CC)C.Br[CH2:46][C:47]([O:49][CH3:50])=[O:48].C(OCC)(=O)C>CN(C=O)C>[CH3:50][O:49][C:47](=[O:48])[CH2:46][NH:1][C@H:2]([C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][C@H:9]([N:12]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][OH:11])[CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 60984Methyl bromoacetateHCID 513930HCID 513930, compound2×

Product 1

HCID 513937HCID 513937, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a stirred solution of (2S,4S)-2-amino-N-{4-[(4-amino-benzenesulfonyl)-isobutyl-amino]-5-hydroxy-pentyl}-3-naphthalen-1-yl-propionamide (product of example 8) (0.023 g, 0.044 mmol) in DMF (0.7 mL) was added triethylamine (12.0 μL, 0.087 mmol) and methyl bromoacetate (4.0 μL, 0.054 mmol). The mixture was stirred to room temperature for 1 h. Ethyl acetate was added and the organic layer was washed with a saturated solution of NaHCO3, then dried with MgSO4 and concentrated. The residue was purified by flash chromatography eluting with a mixture of hexane/EtOAc. The yield obtained was 47%.

Workup

  1. washthe organic layer was washed with a saturated solution of NaHCO3
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography
  5. washeluting with a mixture of hexane/EtOAc
  6. customThe yield obtained

Sources & evidence

ORD record
ord-ef93f63eea034ca79859c4e2887dba0e
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06632816B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes