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Diethylamine → methyl (1S)-1-({[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

HRID 1174114
Notes
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Reaction equation

HRID 1174114 reaction equation
[CH2:1]([C@H:8]([NH:38][C:39]([C@@H:41]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:9][C@H:10]([OH:37])[C@@H:11]([NH:19]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NCC)C>CN(C=O)C>[NH2:19][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@@H:10]([OH:37])[CH2:9][C@@H:8]([NH:38][C:39]([C@@H:41]([NH:46][C:47](=[O:50])[O:48][CH3:49])[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86726165methyl (1S)-1-{[((1S,3S,4S)-1-benzyl-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-hydroxy-5-phenylpentyl)amino]carbonyl}-2,2-dimethylpropylcarbamate

Product 1

HCID 17756282methyl (1S)-1-({[(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl]amino}carbonyl)-2,2-dimethylpropylcarbamateYield 594.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 3C (0.130 g, 0.192 mmol) in DMF (6 mL) was treated with diethylamine (1.5 mL), stirred at 25° C. for 1 hour, and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with a gradient starting with ethyl acetate and ending with methanol to give the title compound (0.52 g, 60% yield).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with a gradient

Sources & evidence

ORD record
ord-0db22f7bfa3046dcb7fc4088a648bd36
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834043B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes