(R,S)-Boc-2-amino-tetradecanoic acid → Tert-butyl n-[1-(r/s)-(hydroxymethyl)tridecyl]carbamate

HRID 970295Notes

Reaction equation

HRID 970295 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 1

HCID 2756016(R,S)-Boc-2-amino-tetradecanoic acid

Product 1

HCID 15673749Tert-butyl n-[1-(r/s)-(hydroxymethyl)tridecyl]carbamateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(R/S)-[(tert-butoxycarbonyl)amino]tetradecanoic acid 41 (1.00 g, 2.92 mmol) in abs. THF (3 ml) was added slowly dropwise to BH3-THF complex (1.0M, 5.8 ml, 5.80 mmol) at 0° C. After stirring for 2 hours, the reaction mixture was quenched with 10% acetic acid in methanol (v/v) and evaporated. The residue was taken up in CH2Cl2 (10 ml) and washed with 1M KHSO4(aq) (1×20 ml) and brine (2×20 ml). The solution was then dried over MgSO4, filtered and evaporated. Purification by column chromatography gave 44 (821 mg, 86%).

Workup

  1. customthe reaction mixture was quenched with 10% acetic acid in methanol (v/v)
  2. customevaporated
  3. washwashed with 1M KHSO4(aq) (1×20 ml) and brine (2×20 ml)
  4. dry with materialThe solution was then dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-b0f4f05998af4534bd38f68ad57a720e
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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