Acetic Acid → Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

HRID 1354521Notes

Reaction equation

HRID 1354521 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19]([OH:21])=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:24])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.C(O)(=O)C>CCOCC>[CH3:24][O:20][C:19](=[O:21])[C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[NH:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6628DiazaldHCID 9550DiazomethaneHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 14427182Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(O-benzyl) Boc Serine 2.00 g (6.8 mmoles) was dissolved in 50 ml of ether. To this solution was added an ether solution containing freshly prepared diazomethane prepared from 5 g of Diazald using the procedure from Aldrich Technical Bulletin number AL-180. After stirring the solution for 30 minutes, glacial acetic acid was added dropwise until the solution became clear. The resulting solution was concentrated in vacuo to yield 2.00 g, 95% as a clear oil. 1H: (CDCl3); 7.3 (d, 5H), 5.5 (bs, 1H), 4.5 (s, 2H), 3.8 (m, 2H), 3.7 (s, 3H), 1.4 (s, 9H)

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. customto yield 2.00 g, 95% as a clear oil

Sources & evidence

ORD record
ord-4ead5d8594c8438888d6852d8f257a08
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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