Triethylamine → alpha-(Tert-butoxycarbonyl)amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid

HRID 1856490Notes

Reaction equation

HRID 1856490 reaction equation
Cl.[NH2:2][CH:3]([C:7]1[C:15]2[CH2:14][S:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:23]([O:27][C:28](N=[N+]=[N-])=[O:29])([CH3:26])([CH3:25])[CH3:24]>O.O1CCOCC1>[C:23]([O:27][C:28]([C:3]([NH2:2])([C:7]1[C:15]2[CH2:14][S:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 70589182alpha-Amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid hydrochloride

Product 1

HCID 86737162alpha-(Tert-butoxycarbonyl)amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

α-Amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid hydrochloride (0.01 m) is dissolved in a mixture of equal parts of water and dioxane. Triethylamine (0.01 m) and tert-butoxycarbonylazide (0.01 m) are added to the mixture which is stirred for 18 hours at room temperature. The dioxane is evaporated from the mixture, ethyl acetate is added and the pH of the aqueous phase is adjusted to about 2.5 with the addition of 1 N hydrochloric acid. The phases are separated and the aqueous phase is extracted a second time with additional ethyl acetate. The ethyl acetate is separated from the aqueous phase. These extracts are combined and dried over magnesium sulfate. Evaporation of the ethyl acetate gives α-(tert-butoxycarbonyl)amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid.

Workup

  1. customThe dioxane is evaporated from the mixture, ethyl acetate
  2. additionis added
  3. additionthe pH of the aqueous phase is adjusted to about 2.5 with the addition of 1 N hydrochloric acid
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted a second time with additional ethyl acetate
  6. customThe ethyl acetate is separated from the aqueous phase
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-7ee08d9303a34a50a6dc5865c11b647d
Source dataset
uspto-grants-1980_08
Patent number
US04219648

Reaction notes

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