4-Methylmorpholine → Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

HRID 2085702Notes

Reaction equation

HRID 2085702 reaction equation
[NH:1]([C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC.O>[CH:24]1[C:23]2[CH:22]([CH2:21][O:20][C:18]([NH:1][C@@H:2]([CH2:15][OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:19])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 13585941(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 11655404Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of Fmoc-D-Lys(BOC)—OH (2.102 g, 4.5 mmol) in DME (5 mL) at −15° C. was treated successively with N-methylmorpholine (0.56 mL, 5.0 mmol) and isobutyl chloroformate (0.7 mL, 5 mmol), stirred for 2 minutes, and filtered. The filter cake was washed with DME (3×5 mL) and the combined filtrate and washings were cooled to −5° C. and treated with NaBH4 (0.3 g, 7.5 mmol) in water (5 mL) and additional water(250 mL) immediately afterwards. The mixture was stirred for 15 minutes and filtered. The filter cake was washed with water and dried to provide the desired product. MS (APCI) m/e 455 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with DME (3×5 mL)
  3. stirringThe mixture was stirred for 15 minutes
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-33f953784954478691fe24259be365a9
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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