Tert-Butylamine → Boc-Thz-NH-tBu

HRID 263659Notes

Reaction equation

HRID 263659 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][S:7][CH2:6][C@H:2]1[C:3]([NH:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:5]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 54130109Boc-Thz-NH-tBuYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 g (12.9 mmol) of Boc-Thz-OH and 2.15 ml (15.5 mmol) of triethylamine in 25 ml of DMF, 2.02 ml (15.5 mmol) of isobutyl chloroformate was added dropwise at -15° C. After stirring for 10 min at that temperature. 4.06 ml (38.7 mmol) of tert-butylamine was added. The reaction mixture was stirred for 10 min at that temperature and 100 min under ice cooling, concentrated under reduced pressure, diluted with 50 ml of ethyl acetate, washed with 5% NaHCO3 aqueous solution, 5% citric acid aqueous solution, and saturated NaCl aqueous solution successively, dried over Na2SO4, and evaporated under reduced pressure to give 3.13 g (Y. 84%) of Boc-Thz-NH-tBu which was convened to Qoa-Mta-AHPBA-Thz-NH-tBu by a similar method with processes 2-5 of Example 3.

Workup

  1. stirringThe reaction mixture was stirred for 10 min at that temperature and 100 min under ice cooling
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with 50 ml of ethyl acetate
  4. washwashed with 5% NaHCO3 aqueous solution, 5% citric acid aqueous solution, and saturated NaCl aqueous solution successively
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7a32289e00f14195b18507ff82a3c4b1
Source dataset
uspto-grants-1997_07
Patent number
US05644028

Reaction notes

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