Hydrochloric Acid → tert-butyl(S)-6-tert-butoxycarbonylamino-2-(2-oxooxazolidine-3-sulfonylamino)hexanoate

HRID 1943304Notes

Reaction equation

HRID 1943304 reaction equation
[NH2:1][C@H:2]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[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].Cl.C(N(CC)CC)C.[O:30]=[C:31]1[N:35]([S:36](Cl)(=[O:38])=[O:37])[CH2:34][CH2:33][O:32]1.Cl>ClCCl>[C:11]([O:10][C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]([NH:1][S:36]([N:35]1[CH2:34][CH2:33][O:32][C:31]1=[O:30])(=[O:38])=[O:37])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 112868832-Oxo-1,3-oxazolidine-3-sulfonyl chlorideHCID 1381988513288-57-8

Product 1

HCID 67028806tert-butyl(S)-6-tert-butoxycarbonylamino-2-(2-oxooxazolidine-3-sulfonylamino)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5.39 g of H-Lys(Boc)-OtBu hydrochloride (15.9 mmol, 1.0 eq) and 7.1 ml of triethylamine (50.9 mmol, 3.2 eq) in dichloromethane (70 ml) was added to the solution obtained in Example 143d), in such a way that the temperatures did not exceed 10° C. After the addition was complete, the mixture was allowed to reach RT and was stirred for a further 2 h. The reaction mixture was then mixed with 200 ml of 0.2 M hydrochloride acid, and the organic phase was separated off and washed with 100 ml of 0.2 M hydrochloric acid and concentrated. 5.5 g of the desired material were obtained as a colorless oil, which crystallized on standing.

Workup

  1. customdid not exceed 10° C
  2. additionAfter the addition
  3. customto reach RT
  4. customthe organic phase was separated off
  5. washwashed with 100 ml of 0.2 M hydrochloric acid
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2dc38d04f59047c0b83ee12d15b2743d
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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