5-Aminovaleric acid → FMOC-5-AMINOPENTANOIC ACID

HRID 344656Notes

Reaction equation

HRID 344656 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:16]([O:18][CH2:19][CH:20]1[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17]>O.O1CCCC1>[CH:31]1[C:32]2[CH:20]([CH2:19][O:18][C:16]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:17])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 1385-Aminovaleric acidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 2756098FMOC-5-AMINOPENTANOIC ACID

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.00 g 5-aminopentanoic acid and 3.62 g of sodium carbonate in 30 ml of water was cooled to 0° C. and 4.41 g of 9-fluorenylmethyl chloroformate in 10 ml of tetrahydrofuran was added dropwise. The mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was then diluted with water and washed with ether. The aqueous solution was cooled to 0° C. and adjusted to pH 2 with 3N hydrochloric acid. The resulting white solid was collected by filtration and dried to give N-(9-fluorenylmethoxycarbonyl)-5-amino-pentanoic acid.

Workup

  1. washwashed with ether
  2. temperatureThe aqueous solution was cooled to 0° C.
  3. filtrationThe resulting white solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-8f7e7d4cbdb64c7ebc90f1d075cd96b3
Source dataset
uspto-grants-1991_10
Patent number
US05053392

Reaction notes

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