Triethylamine → (2S)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 1003283Notes

Reaction equation

HRID 1003283 reaction equation
[CH2:1]([O:8][C:9]1[CH:19]=[CH:18][C:12]([C@H:13]([OH:17])[C:14]([OH:16])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[NH2:21][C@H:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][C:26]([OH:32])=[CH:27][CH:28]=2)[CH2:23]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:13]([OH:17])[C:14]([NH:21][C@H:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][C:26]([OH:32])=[CH:27][CH:28]=3)[CH2:23]2)=[O:16])=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 54160087HCID 54160087, compoundHCID 69543637(S)-2-amino-7-hydroxytetralin hydrobromide

Product 1

HCID 57222877(2S)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamideYield 93.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-4-Benzyloxymandelic acid (1.80 g), (S)-2-amino-7-hydroxytetralin hydrobromide (1.87 g) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (3.39 g) were dissolved in N,N-dimethylformamide (21 ml), and triethylamine (2.03 ml) was added to the solution under ice-cooling with stirring. After reaction at room temperature for an hour, diethyl ether and water were added to the reaction mixture. Collection by filtration of the resulting precipitates gave (2S)-2-(4-benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (2.64 g) as powders.

Workup

  1. temperaturecooling
  2. customAfter reaction at room temperature for an hour
  3. customCollection
  4. filtrationby filtration of the resulting
  5. customprecipitates

Sources & evidence

ORD record
ord-6411bbf9f88443dcaab1ab166c515154
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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