Triethylamine → tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate

HRID 2222987Notes

Reaction equation

HRID 2222987 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:19]([O:20][CH3:21])[CH3:18])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protectedHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 58604314tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamateYield 138.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-tert-Butoxycarbonylamino-thiazole-4-carboxylic acid (10.44 g, 42.74 mmol), N,O-dimethylhydroxylamine hydrochloride (5.0 g, 51.26 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (9.83 g, 51.28 mmol), 1-hydroxybenzotriazole hydrate (6.93 g, 51.28 mmol), triethylamine (7.15 ml, 51.28 mmol) and 4-(dimethylamino)pyridine (1.04 g, 8.52 mmol) were combined in dichloromethane (200 mL) and stirred overnight at room temperature. The resulting solution was poured into ethyl acetate and washed with 0.2 M aqueous hydrochloric acid, water, brine and dried over magnesium sulfate. Solvent was removed and the crude was by purified over silica gel eluted with 80% v/v ethyl acetate in hexane to give [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester as a foam (17.0 g, 95%).

Workup

  1. washwashed with 0.2 M aqueous hydrochloric acid, water, brine
  2. dry with materialdried over magnesium sulfate
  3. customSolvent was removed
  4. customby purified over silica gel
  5. washeluted with 80% v/v ethyl acetate in hexane

Sources & evidence

ORD record
ord-a5f008ba59ba4effa0c9ef5c73663f18
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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