Tetrahydrofuran → HCID 86738444, compound

HRID 1156741Notes

Reaction equation

HRID 1156741 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:14]([OH:16])=O)[CH2:12][OH:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2N=[N:20]1.C1([N:34]=C=NC2CCCCC2)CCCCC1.[O:43]1[CH2:47]CCC1>>[N:19]#[N:20].[C:1]1([CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:34][O:43][CH2:47][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:12][OH:13])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 13817628N-(Phenylacetyl)-L-serine

Product 1

HCID 86738444HCID 86738444, compound

Conditions

Temperature
0 °C

Procedure

N-Phenylacetyl-L-serine (8.8 g), 1-hydroxybenzotriazole hydrate (6.03 g) and o-benzylhydroxylamine (4.84 g) are dissolved in tetrahydrofuran (450 ml) and chilled to 0° C. A solution of dicyclohexylcarbodiimide (8.1 g), in tetrahydrofuran (50 ml) is added over a 0.5 hour period. The reaction is allowed to warm to 26° C. and stir for about 16 hours. The mixture is filtered, and the filtrate concentrated under reduced pressure to a semi-solid residue. The addition of ethyl acetate (50 ml) causes crystallization. The solids are collected and dried (6.9 g, melting point 150°-151° C.).

Workup

  1. temperatureto warm to 26° C.
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure to a semi-solid residue
  4. additionThe addition of ethyl acetate (50 ml)
  5. customcrystallization
  6. customThe solids are collected
  7. customdried (6.9 g, melting point 150°-151° C.)

Sources & evidence

ORD record
ord-2dc3c673799a41ff84bf2350a9920db8
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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