Ammonia → (S)-tert-Butyl (1-amino-3-(4-iodophenyl)-1-oxopropan-2-yl)carbamate

HRID 216901Notes

Reaction equation

HRID 216901 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:23]1CCOCC1)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N>CN(C=O)C.O>[NH2:23][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 57999635(S)-tert-Butyl (1-amino-3-(4-iodophenyl)-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-2-(tert-Butoxycarbonylamino)-3-(4-iodophenyl)propanoic acid (35.1 g) was dissolved in DMF (200 mL) and to the resulting solution was added N-ethylmorpholine (17.0 mL) followed by TBTU (28.8 g). The mixture was stirred at room temperature for 0.5 h and then cooled to 0° C. 0.88 Ammonia (11.1 mL) was added and the mixture was allowed to warm to room temperature. The mixture was allowed to stir at room temperature for 16 h and was then poured into water and the resulting precipitate removed by filtration. The solid was dried in vacuo to give the sub-titled compound (34.2 g).

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringto stir at room temperature for 16 h
  4. customthe resulting precipitate removed by filtration
  5. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-8524e3ad3217460c9337096cf08bca27
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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